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CAS No. : | 73-24-5 | MDL No. : | MFCD00041790 |
Formula : | C5H5N5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GFFGJBXGBJISGV-UHFFFAOYSA-N |
M.W : | 135.13 | Pubchem ID : | 190 |
Synonyms : |
6-Aminopurine;Vitamin B4;NSC 14666
|
Chemical Name : | Purin-6-amine |
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 36.09 |
TPSA : | 80.48 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.5 cm/s |
Log Po/w (iLOGP) : | 0.53 |
Log Po/w (XLOGP3) : | -0.53 |
Log Po/w (WLOGP) : | -0.06 |
Log Po/w (MLOGP) : | -0.82 |
Log Po/w (SILICOS-IT) : | 0.47 |
Consensus Log Po/w : | -0.08 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.01 |
Solubility : | 13.2 mg/ml ; 0.0977 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.69 |
Solubility : | 27.5 mg/ml ; 0.204 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.77 |
Solubility : | 2.27 mg/ml ; 0.0168 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.67 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P301+P310 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.5 g | Stage #1: With sodium hydroxide In water at 100 - 110℃; for 5 h; Stage #2: With ammonium chloride In water at 25℃; |
Example: 6 Preparation of 9-[2-(R)-(Hydroxy)propyl]adenine (I) Method-A Sodium hydroxide (3 g) was added to a stirred suspension of adenine (10 g) in water (50 ml) at room temperature, and the reaction mixture was heated to 100-1 10°C. After 5 hrs at this temperature, the reaction mixture was allowed to cool down to 25°C. Ammonium chloride (3.96 g) and 2-(R)- (+) propylene oxide (6.44 g) were added in succession to the reaction mixture at this temperature. The reaction mixture was maintained at this temperature until the reaction was complete as indicated by TLC. The reaction mixture was concentrated under reduced pressure at 55°C to furnish the desired product, contaminated with unidentified polar impurities. The crude material was purified by column chromatography using a solvent system comprising of methanol and dichloromethane (1 : 9) as the eluant to furnish 9-[2-(R)- (hydroxyl)propyl]adenine as a white solid; yield: 5.5 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide;tetrabutylammomium bromide; In water; benzene; at 80 - 83℃; for 12h; | Example 2: Synthesis of urin-6-ylamine To a suspension of <strong>[73-24-5]adenine</strong> (3 g, 22.22 mmol) in benzene (55.5 mL) was added sodium hydroxide solution (9.8 mL of 10%) followed by the addition of tetra n-butyl ammonium bromide (1.430 g, 4.44 mmol). To the resulting reaction mixture, benzyl chloride (4.21 g, 3.8 mL, 33.3 mmol) was added under constant stirring. The reaction mixture was heated in an oil bath maintained at about 80-83 C for 12 hours. The reaction mixture was cooled to room temperature to yield a crude organic compound, which was purified by column chromatography using methanol : ethyl acetate solvent mixture as an eluent. Yield = 1. 5 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | A mixture of 3-bromo-l-phenylpropane-l,2-dione (1.0 g, 4.42 mmol), <strong>[73-24-5]adenine</strong> (590 mg, 4.42 mmol) and 2,3-diaminotoluene (540 mg, 4.42 mmol) in EtOH (2OmL) was heated at 6O0C for 4 h. After cooling, the reaction mixture was partitioned between EtOAc and water. The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by preparative etaPLC (Method 1) to give the title compound (23 mg, 14%) as an off-white solid. deltaeta (DMSO-d6) 8.46 (s, IH), 7.88-8.05 (m, 4H), 7.59-7.72 (m, 6H), 7.53 (s, IH), 5.94 (s, 2H), 2.74 (s, 3H). LCMS (ES+) 368.2 (M+H)+, RT 2.15 minutes (Method 3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4% | A mixture of Intermediate 5 (113 mg, 0.37 mmol) and <strong>[73-24-5]adenine</strong> (51 mg, 0.37 mmol) in DMF (4 mL) was sonicated for 40 minutes at 4O0C then stirred at r.t. for 18 h. <n="107"/>More <strong>[73-24-5]adenine</strong> (51 mg, 0.37 mmol) was added and the reaction heated to 800C for 1 h. Purification by preparative HPLC {Method 1) gave the title compound as a pale yellow solid (5 mg, 4%). deltaH (DMSO-d6) 8.00-8.10 (m, 2H), 7.85-7.95 (m, 3H), 7.75-7.85 (m, IH), 7.50-7.70 (m, 5H), 7.20-7.30 (m, 2H), 5.55 (s, 2H). LCMS (ES+) 353.2 (M+H)+, RT 1.94 minutes {Method 3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | In N,N-dimethyl-formamide; at 80℃; for 1.5h; | A mixture of Intermediate 61 (98 mg, 0.3 mmol) and <strong>[73-24-5]adenine</strong> (81 mg, 0.6 mmol) in DMF (3 mL) was stirred at 8O0C for 90 minutes. Purification by preparative etaPLC {Method 2) gave the title compound as a white solid (6 mg, 6%). deltaeta (DMSO-d6) 8.30 (s, IH), 8.16 (s, IH), 7.66-7.69 (m, IH), 7.55-7.59 (m, IH), 7.26-7.49 (m, 5H), 7.09 (s, IH), 5.53 (br s, 2H), 5.34 (s, 2H), 2.75 (s, 3H), 2.04 (s, 3H). LCMS (ES+) 381.2 (M+H)+, RT 3.37 minutes {Method 4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18.5h;sonication; | A mixture of Intermediate 7 (156 mg, 0.5 mmol), <strong>[73-24-5]adenine</strong> (74 mg, 0.55 mmol) and K2CO3 (76 mg, 0.55 mmol) in DMF (4 mL) was sonicated for 30 minutes then stirred at r.t for 18 h. Purification by preparative etaPLC {Method 1) gave the title compound as a white solid (75 mg, 41%). deltaeta (DMSO-d6) 8.02 (s, IH), 7.89 (s, IH), 7.88 (s, IH), 7.75 (d, J 8 Hz, IH), 7.68-7.69 (m, 2H), 7.62 (d, J 8 Hz, IH), 7.42-7.56 (m, 4H), 7.24 (s, 2H), 5.60 (s, 2H), 2.70 (s, 3H). LCMS (ES+) 367.2 (M+H)+, RT 3.27 minutes {Method 4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In N,N-dimethyl-formamide; at 40 - 80℃; for 1.5h;sonication; | A mixture of Intermediate 9 (82 mg, 0.26 mmol) and <strong>[73-24-5]adenine</strong> (70 mg, 0.52 mmol) in DMF (3 mL) was sonicated for 30 minutes at 400C then stirred at 800C for 1 h. Purification by preparative etaPLC (Method 2) gave the title compound as a white solid (40 mg, 42%). deltaeta (DMSOd6) 8.00 (s, IH), 7.70-7.85 (m, 4H), 7.59-7.61 (m, 2H), 7.40-7.48 (m, 2H), 7.15-7.25 (m, 4H), 5.26 (s, 2H), 1.79 (s, 3H). LCMS (ES+) 367.1 (M+H)+, RT 2.41 minutes (Method 4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24%; 41% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26%; 23% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36%; 41% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54%; 23% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26%; 38% | With potassium carbonate; In N,N-dimethyl-formamide; at 130℃; for 0.5h;Microwave irradiation; | General procedure: A mixture of <strong>[73-24-5]adenine</strong> (1 equiv.), the corresponding monocationic intermediate (1 equiv.) and K2CO3 (2 equiv.) in DMF (4 mL) was microwave-irradiated at a set temperature of 130 C for 30 min. Solvent was evaporated and the crude product was purified by flash column chromatography using as eluent CH2Cl2/methanol (10/0.5?7/3) to afford 8-20. The discrimination between N-9 and N-3 substituted derivatives has been clarified through the HMBC experiment to three bonds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 10 - 20℃;Inert atmosphere; | General procedure: To a dioxane solution (4.5 mL) of 3 (160 mg, 0.417 mmol), purine (0.627 mmol), and triphenylphosphine (164 mg, 0.627 mmol) under argon at 10 C was added dropwise di-isopropylazodicarboxylate (127 mg, 0.627 mmol). After 12 h stirring at room temperature, volatiles were evaporated, and residue was purified by silica gel column chromatography (MeOH/CH2Cl2 2:98) to give pure desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | Example 8 Preparation of Zoledronic, Adenine, and Water Complex by Solvent-Drop Grinding 96 mg of zoledronic acid is ground with 65 mg of adenine and 60 muL of water is added to the solid mixture. The solids gathered after grinding are stored. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In ethanol; for 6h;Dean-Stark; Reflux; | Schiff base ligand (1) was prepared by taking <strong>[73-24-5]adenine</strong> and Para-hydroxyl benzaldehyde in ethanol and pouring in a three neck round bottom flask equipped with a reflux condenser, thermometer and a Deane-Stark funnel. The above reaction mixture was heated under reflux for 6 h. Water formed during the reaction was removed through Deane-Stark funnel. The solvent was removed under reduced pressure. The resulting white solid was recrystallized from chloroform. Yield: 87%; m.p: 131-133 C; Mol. Formula: C12H9N5O; Mol. wt. 239.23. Elemental analysis: For C12H9N5O, Anal. calcd(%): C, 60.25; H, 3.79; N, 29.27, found (%): C, 59.98; H, 3.74; N,29.20; IR (KBr): 3285br (nu O-H); 3085sr (nu C-H); 2895br (nu N-H); 1565sr (nu C=N). 1H NMR (CDCl3): delta 4.5s (1H, 1 hydroxyl); 6.4m (2H, aromatic); 6.9m (2H, aromatic); 7.4d (1H, Imidazole); 8.8s (1H, Azomethanic); 9.4s (1H, pyrimidinic); 10.2d (1H, Imidazole). 13C NMR (CDCl3): delta C2 = 157.5; C4 = 121.7; C5 = 110.8; C6 = 175.4; C9 = 134.6; C11 = 118.6; C12 = 128.2; C13 = 118.7; C14 = 155.4; C15 = 112.7; C16 = 129.3; C18 = 167.5. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | at 20 - 100℃; for 72h; | Isophthalic acid (H2ipa, 166 mg,1 mmol), <strong>[73-24-5]adenine</strong> (Had, 135 mg, 1 mmol), Cd(NO3)2 4H2O (462 mg, 1 mmol) and tetraethylammonium bromide (220 mg, 1 mmol)were added to 4 mL DMA (N,N-dimethylacetamide) and 1.5 mL MeOH (methanol)mixed solvents, and then the solution was placed in a 20 mL vial and stired at room temperature for 1h. The mixture was heated at 100 C for 3 days, and then cooled slowly to room temperature over 4h. Colourless rod-like crystals of the product were formed and collected by filtration and washed with DMA several times. (Yield: 65%based on H2ipa). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With triethylamine; In ethanol; chloroform; for 6h;Reflux; | For the synthesis of ligand (L) <strong>[73-24-5]adenine</strong> (0.2 mM) was suspended in chloroform (15 ml) and neutralized with triethylamine. Ethanolic solution of L-histidine (0.2 mM)was added to the above solution and the resultant mixture was refluxed for 6 h. The solid product formed was filtered and washed with chloroform. The filtrate together with the washings were treated with citric acid solution (10 %,10 ml) and with water. The organic layer was separated.After drying over anhydrous CaCl2, the solvent was removed by evaporation to obtain the ligand. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.5 g | Example: 6 Preparation of 9-[2-(R)-(Hydroxy)propyl]adenine (I) Method-A Sodium hydroxide (3 g) was added to a stirred suspension of adenine (10 g) in water (50 ml) at room temperature, and the reaction mixture was heated to 100-1 10C. After 5 hrs at this temperature, the reaction mixture was allowed to cool down to 25C. Ammonium chloride (3.96 g) and 2-(R)- (+) propylene oxide (6.44 g) were added in succession to the reaction mixture at this temperature. The reaction mixture was maintained at this temperature until the reaction was complete as indicated by TLC. The reaction mixture was concentrated under reduced pressure at 55C to furnish the desired product, contaminated with unidentified polar impurities. The crude material was purified by column chromatography using a solvent system comprising of methanol and dichloromethane (1 : 9) as the eluant to furnish 9-[2-(R)- (hydroxyl)propyl]adenine as a white solid; yield: 5.5 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.42 g | Example: 11 Preparation of 9-[2-(R)-(phosphonomethoxy)propyl] <strong>[73-24-5]adenine</strong> (II). Method-A Magnesium di-tert-butoxide (51 mg) was added to a stirred suspension of <strong>[73-24-5]adenine</strong> (2 g) in methanol (12 ml) at 10C. After 4 h at this temperature, sodium hydroxide (12 mg) and (R)-(+)-propylene oxide (1 .25 g) were added in succession to the reaction mixture. The reaction mixture was allowed to warm to room temperature and stirred at this temperature until the reaction was complete, as indicated by TLC. Methanol was evaporated under vacuum. N, N-Dimethylformamide (16 ml) was added to the crude reaction mixture thus obtained and the mixture was heated to 60-70C. Magnesium di-tert-butoxide (7 g) was added to the reaction mixture in four divided batches over a period of 15 minutes at this temperature. The mixture was heated to 80-90C, and stirred at this temperature for 30 minutes. Diethyl p-toluenesulfonyloxymethylphosphonate (13.2 g) was added drop by drop to the reaction mixture over a period of 4 h, and the mixture was stirred at this temperature until the reaction was complete, as indicated by TLC. N, N-Dimethylformamide was distilled out under vacuum at 90-100C. Aqueous hydrobromic acid (48% w/w, 30 ml) was then added to the residue and the reaction mixture was heated to gentle reflux. After approximately 20 h at this condition, the reaction mixture was allowed to cool down to room temperature and filtered. The filtered solid was washed with dichloromethane (10 ml). The washing was concentrated to furnish a residue. The residue was combined with the filtrate and the combined filtrate was washed with dichloromethane (2 X 10 ml). To the aqueous layer, an aqueous solution of sodium hydroxide (50 %) was added until the pH attained 2.1 -3. After several hours at room temperature, the aqueous layer was cooled to 0- 5C and stirred at this temperature for further hours to maximize precipitation of the desired product from the solution. The precipitated solid was filtered, washed with cold water (1 X 5 ml), acetone (2X 5 ml) and dried to obtain 9-[2-(R)-(phosphonomethoxy)propyl]<strong>[73-24-5]adenine</strong>; yield: 1 .42 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With purine nucleoside phosphorylase; uridine phosphorylase; In aq. phosphate buffer; at 60℃; for 1.5h;Enzymatic reaction; | Transglycosylation reaction was carried out at analytical scale in the followingconditions: 250 ml of cell lysates (equivalent to 14 units of each UPase and PNPase enzymatic activities) was added to10 ml of a solution having the following composition: 4 mM 1-beta-D-ribofuranosyluracil (uridine nucleoside), 4 mM <strong>[73-24-5]adenine</strong>base, 30 mM potassium phosphate buffer pH 7, thermostatically controlled at 60C. After 1.5 hours at 60C, the reactionwas stopped by diluting the mixture 1:5 and cooling in ice. The percentage of bioconversion of <strong>[73-24-5]adenine</strong> base to 9-beta-Dribofuranosyl<strong>[73-24-5]adenine</strong>(adenosine nucleoside) was determined by analyzing an aliquot of the reaction mixture by highperformance liquid chromatography (HPLC) with the use of Kromasil 100-5C18 (Akzo Nobel) column of a size of 250 x4.6mm and eluted with a 4% methanol-water solution. The transglycosylation catalytic activity was expressed as units· ml -1 (mmoles ofAra-A formed in 1.5 hours · ml -1 of mixture of cell lysates) or in units · g -1 of moist resin (mmoles ofD-ribofuranosyl<strong>[73-24-5]adenine</strong> formed in 1.5 hours · ml -1 of cell lysate) and was calculated relative to a standard D-ribofuranosyl<strong>[73-24-5]adenine</strong>solution eluted by HPLC in the same conditions. Under these conditions, about 55 percent of adenosinenucleoside was formed (approximately 9 units per ml of cell lysate). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.8% | at 140 - 150℃; for 4h; | 10 mL of formamide and 90 g of <strong>[118-70-7]4,5,6-triaminopyrimidine</strong> (Formula 6) were added to a 1000 mL reaction flask and heated to 140 to 150 C for 4 hours. The reaction was completed and cooled to a temperature of 25 to 15 C Crystallization, filtration, formamide rinsing, water elution, gray adipate crude, refined with water, activated carbon decolorization after 79.5g white crystalline powder adenine (Formula 1), yield 81.8%, HPLC 99.9%. |
81.8% | at 140 - 150℃; for 4h; | 10 mL of formamide and 90 g of <strong>[118-70-7]4,5,6-triaminopyrimidine</strong> (Formula 6) were added to a 1000 mL reaction flask and heated to 140 to 150 C for 4 hours. The reaction was completed and cooled to a temperature of 25 to 15 C for crystallization, filtration, formamide rinsing, water elution, the crude gray adenine, water purification, activated carbon decolorization. 79.5g white crystalline powder adenine (Formula 1), the yield of 81.8%, HPLC 99.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | The ester derivative of <strong>[73-24-5]adenine</strong> was synthesized by modified reported procedure [4]. Adenine (3.0 g, 22.20 mmol) was dissolved in dry DMF 50 mL followed by the addition of anhydrous potassium carbonate (1.01 g, 44.40 mmol) under N2 atmosphere at temperature 0 C. After 1 hr, methyl bromoacetate (3.70 mL, 33.0 mmol) was slowly added in to the reaction mixture, the reaction was stirred for 24 hours. The reaction was monitored by thin layer chromatography, solvent was evaporated at 70 0C under reduced pressure and the reaction mixture was purified by the column chromatography. The white powder product was eluted by using 2 % (methanol/DCM). (50 % yield). HRMS: (M+H)+ calculated: 208.0835, observed: 208.0835. 1H NMR: (500 MHz, DMSO-d6, 25 C, TMS) delta (ppm) 3.76 (s, 3H, -OCH3), 4.94 (t, 2H.-CH2-), 6.90 (s, 2H, N6-H), 7.84 (s, 1H, C2-H), 8.05 (s, 1H, C8-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In N,N-dimethyl-formamide; at 125 - 138℃; | Step 4. (R)-9-[2-(diethylphosphonomethoxy)propyl]adenine: In a reactor containing an inert atmosphere, for example nitrogen, adenine (1.0 kg),A mixture of sodium hydroxide (11.8 g), (R) -1,2-propylene carbonate (0.83 kg), and N, N-dimethylformamide (6.5 kg) was treated with about 0.5% area normalized HPLC, Indicating that the adenine remained unresolved until the reaction was completed,Heat to 130 C (typically about 125-138 C) for about 18-30 hours. The resulting mixture is cooled to about 25 C. (typically about 20 to 30 C.) and contains a Stage I intermediate, (R) -9- (2-hydroxypropyl) adenine, It can precipitate at this point. After cooling, lithium t-butoxide (3.62 kg), 2.0 M in tetrahydrofuran was added to stage I intermediate to produce the lithium salt of (R) -9- (2-hydroxypropyl) adenine in a mild exothermic reaction . The slurry was treated with diethyl p-toluenesulfonyloxymethyl phosphonate (1.19 kg) and the mixture was heated to a temperature of about 32 C. (typically about 30 to 45 C.) and heated for at least about 2 hours (Typically about 2 to 3 hours) Meanwhile, the mixture becomes uniform. Further diethyl p-toluenesulfonyloxymethylphosphonate (1.43 kg) is added and the mixture is heated at a temperature of about 32 C. (typically about 30-45 C.) for at least about 2 hours (typically about 2- 3 hours). Further lithium t-butoxide (0.66 kg), 2.0 M in tetrahydrofuran and diethyl p-toluenesulfonyloxymethylphosphonate (0.48 kg) were added two more times and after each time the mixture was added at a temperature of about 32 C. for at least about 2 hours Stir. Completion of the reaction is monitored by indicating that area normalized HPLC, if necessary, shows only 10% residual Stage I intermediate. If the reaction is incomplete, additional lithium t-butoxide (0.33 kg), 2.0 M in tetrahydrofuran and diethyl p-toluenesulfonyloxymethylphosphonate (0.24 kg) are added and the reaction mixture is heated at a temperature of about 32 C. Maintain reaction completion by maintaining for at least about 2 hours. The mixture is then cooled to about 25 C (typically about 20-40 C) and then glacial acetic acid (0.5 kg) is added. The resulting mixture is concentrated in vacuo at a final maximum mixture temperature of about 80 C., under a vacuum of about 29 inches Hg (in Hg). The residue is cooled to about 50 C. (typically about 40-60 C.) and water (1.8 kg) is added and the reaction is rinsed into additional water (1.8 kg). The solution is continuously extracted with dichloromethane (about 35 kg) for 12 to 48 hours and periodically glacial acetic acid (0.2 kg) is added to the aqueous phase after about 5 hours and about 10 hours after the continuous extraction time. Completion of extraction can be achieved by showing that the area-normalized HPLC shows that the residual amount of (R) -9- [2-diethylphosphonomethoxy) propyl] adenine in the aqueous phase is only about 7% It is confirmed. The combined dichloromethane extracts are first concentrated at atmospheric pressure and then in vacuo at extraction temperature at a temperature of only about 80 C. to give the title compound as a viscous orange oil. The title compound yield is about 40-45% by weight (normalized HPLC) and its purity is typically 60-65% by area normalized HPLC. The actual weight of the title compound after concentration is approximately 1.6 times the stoichiometric amount (ie, 3.8 times the expected yield). The additionally observed weight is due to impurities and / or solvents remaining after continuous extraction and concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 90℃; for 16h;Sealed tube; | [00123] A mixture of heptadecan-9-yl 8-((3-chloropropyl)(8-(nonyloxy)-8- oxooctyl)amino)octanoate (500 mg, 0.67 mmol), <strong>[73-24-5]adenine</strong> (135 mg, 1.0 mmol) and 1,8- diazabicycloundec-7-ene (137 mu, 1.0 mmol) in 2 mL DMF was heated at 90 C in a sealed tube for 16 h. The reaction mixture was concentrated to dryness and partitioned between dichloromethane and water. The organic layer was washed with brine. After it was dried over sodium sulfate, the filtrate was concentrated and purified by ISCO (SiC : MeOH/CH2Ch/l% NH4OH 0 to 5%) to afford the product as a yellow oil (325 mg, 57%). LC/UV (202 nm): RT = 8.47 min. MS (APCI): m/z (MH+) 841.7. NMR (300 MHz, CDCb) delta: ppm 8.36 (s, 1H); 7.80 (s, 1H); 5.51 (bs, 2H); 4.85 (p, 1H, J= 6.0 Hz); 4.24 (t, 2H, J= 7.0 Hz); 4.04 (t, 2H, J = 6.6 Hz); 2.45-2.24 (m, 10H); 2.01 (p, 2H, J= 6.9 Hz); 1.68-1.17 (m, 62H); 0.86 (m, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a 500 mL glass vessel equipped with a stirrer, condenser and a thermometer probe were added the Formula II (10.0 g, 0.0254 mol, 1.00 equiv.), Formula III (30.0 mL, 3.00 vol) and N, N-dimethyl acetamide (10.0 mL, 1.00 vol) and the mass was heated to 75±5 C. The reaction mass was maintained at 75±5 C under stirring. The reaction mass was cooled to 25±5 C and Adenine (5.14 g, 0.038 mol, 1.50 equiv.) was added to the reaction mass at 25±5 C under stirring. Methanol (300 mL, 30.0 vol) was added to the reaction mass at constant rate at 25±5 C under stirring. The mass was heated to 60±2 C and the resulting suspension was maintained at the same temperature under stirring. The mass was cooled to 25±5 C and maintained at the same temperature. Water (130 mL, 13.0 vol) was added to the reaction mass at a constant rate under stirring. The reaction mass was maintained at 25±5 C. The mass was filtered and the solid was washed with Methanol (70.0 mL, 7.00 vol), suck dried and dried at 50±5 C under vacuum to obtain Dasatinib-Adenine co-crystal of Formula lb as a crystalline solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | General procedure: To a stirred solutionof carboxylic acid 17 (1.42 mmol) in DMF (13 mL) was added underargon N,N0-carbonyldiimidazole (1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or 2a (1.5 eq.). The reactionmixture was stirred at 100 C until the starting material disappeared(checked by HPLC). Solvent was removed under reducedpressure and column chromatography of the crude materials onreverse phase (RP18, gradient: water to acetonitrile 100%) gave theexpected ethylphosphonate which was passed through a DowexNa ion exchange column. The desired fractions were collected andfreeze dried leading to the desired compounds 18 or 19 as sodiumsalt. 4.5.3.8. Sodium ethyl ((4-(3'-((7H-purin-6-yl)carbamoyl)-[1,1'-biphenyl]-3-yl)-1H-imidazol-1-yl) methyl) phosphonate (18).Yield 63%; 1H NMR (DMSO-d6): d 1.03 (t, J 7 Hz, 3H), 3.65 (q,J 7 Hz, 2H), 3.89 (d, J 12 Hz, 2H), 7.40e8.47 (m,10H), 8.53 (s, 1H),8.75 (s, 1H), 11.80 (bs, 1H), 12.5 (bs, 1H); 13C NMR (DMSO-d6): delta 16.9 (d, 3J 6 Hz), 44.7 (d, 1J 137 Hz), 59.2 (d, 2J 5.7 Hz),117.5, 122.5, 123.7, 124.5, 126.0, 127.6, 129.2, 130.8, 135.8, 139.1,139.5, 140.5, 146.1, 151.2, 166.5; 31P NMR (DMSO-d6): delta 8.35; MS(ESI) m/z 504 [M-Na2H]; HRMS: calcd for C24H23N7O4P [MNa2H] 504.1468, found 504.1549. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium hydride; In N,N-dimethyl-formamide; at 50℃; for 17h;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. 4.5.1.1. 7-Benzyl-7H-<strong>[73-24-5]adenine</strong> (1a). Yield 20%; white powder; 1HNMR (DMSO-d6): delta 5.50 (s, 2H), 7.29-7.36 (m, 3H), 7.44-7.46 (m,2H), 7.75 (s, 1H), 7.95 (bs, 2H), 8.55 (s, 1H); MS (ESI) m/z 226.0[MH]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | General procedure: To a stirred solution of carboxylic acid 23a-e (400 mg, 1.5 mmol)in DMF (15 mL) was added under argon N,N0-carbonyldiimidazole(1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or N-9substituted <strong>[73-24-5]adenine</strong> 4 (3 eq.). The reaction mixture was stirred at100 C until HPLC revealed that the starting material wasconsumed. Volatiles were removed under reduced pressure. Excessof <strong>[73-24-5]adenine</strong> was precipitated in isopropanol, filtered off and thefiltrate was evaporated. The residue was firstly purified by silica gelcolumn chromatography (CH2Cl2/EtOH/AcOH,90/5/5, v/v/v) andthen on reverse phase (RP18 using a gradient of water to methanolcontaining 1% AcOH) to provide the desired compounds. 4.5.7.1. N-(9H-Purin-6-yl)-4'-(2H-tetrazol-5-yl)-[1,10-biphenyl]-2-carboxamide (24a). Yield 15%; 1H NMR (DMSO-d6): delta 7.07-8.09(m, 9H), 8.40 (s, 1H), 8.57 (s, 1H), 11.49 (bs, 1H) 13C NMR (DMSO-d6):delta 126.5, 127.7, 129.2, 130.2, 130.5, 131.2, 135.4, 139.8, 140.2, 146.4,151.6, 152.9, 159.5, 169.8 MS (ESI-) m/z 765.2 [2M-H]-, 382.1 [M-H]-,MS (ESI) 767.3 [2 MH] 384.1 [MH]; HRMS: calcd forC19H14N9O [MH] 384.1321, found 384.1324; HPLC tR 9.16 min,100%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | General procedure: To a stirred solution of carboxylic acid 23a-e (400 mg, 1.5 mmol)in DMF (15 mL) was added under argon N,N0-carbonyldiimidazole(1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or N-9substituted <strong>[73-24-5]adenine</strong> 4 (3 eq.). The reaction mixture was stirred at100 C until HPLC revealed that the starting material wasconsumed. Volatiles were removed under reduced pressure. Excessof <strong>[73-24-5]adenine</strong> was precipitated in isopropanol, filtered off and thefiltrate was evaporated. The residue was firstly purified by silica gelcolumn chromatography (CH2Cl2/EtOH/AcOH,90/5/5, v/v/v) andthen on reverse phase (RP18 using a gradient of water to methanolcontaining 1% AcOH) to provide the desired compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | General procedure: To a stirred solution of carboxylic acid 23a-e (400 mg, 1.5 mmol)in DMF (15 mL) was added under argon N,N0-carbonyldiimidazole(1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or N-9substituted <strong>[73-24-5]adenine</strong> 4 (3 eq.). The reaction mixture was stirred at100 C until HPLC revealed that the starting material wasconsumed. Volatiles were removed under reduced pressure. Excessof <strong>[73-24-5]adenine</strong> was precipitated in isopropanol, filtered off and thefiltrate was evaporated. The residue was firstly purified by silica gelcolumn chromatography (CH2Cl2/EtOH/AcOH,90/5/5, v/v/v) andthen on reverse phase (RP18 using a gradient of water to methanolcontaining 1% AcOH) to provide the desired compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | General procedure: To a stirred solution of carboxylic acid 23a-e (400 mg, 1.5 mmol)in DMF (15 mL) was added under argon N,N0-carbonyldiimidazole(1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or N-9substituted <strong>[73-24-5]adenine</strong> 4 (3 eq.). The reaction mixture was stirred at100 C until HPLC revealed that the starting material wasconsumed. Volatiles were removed under reduced pressure. Excessof <strong>[73-24-5]adenine</strong> was precipitated in isopropanol, filtered off and thefiltrate was evaporated. The residue was firstly purified by silica gelcolumn chromatography (CH2Cl2/EtOH/AcOH,90/5/5, v/v/v) andthen on reverse phase (RP18 using a gradient of water to methanolcontaining 1% AcOH) to provide the desired compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With dmap; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere; | General procedure: To a stirred solution of carboxylic acid 23a-e (400 mg, 1.5 mmol)in DMF (15 mL) was added under argon N,N0-carbonyldiimidazole(1.5 eq.), N,N-dimethyl-4-aminopyridine (0.2 eq.), <strong>[73-24-5]adenine</strong> or N-9substituted <strong>[73-24-5]adenine</strong> 4 (3 eq.). The reaction mixture was stirred at100 C until HPLC revealed that the starting material wasconsumed. Volatiles were removed under reduced pressure. Excessof <strong>[73-24-5]adenine</strong> was precipitated in isopropanol, filtered off and thefiltrate was evaporated. The residue was firstly purified by silica gelcolumn chromatography (CH2Cl2/EtOH/AcOH,90/5/5, v/v/v) andthen on reverse phase (RP18 using a gradient of water to methanolcontaining 1% AcOH) to provide the desired compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; | General procedure: To a stirred solution of <strong>[73-24-5]adenine</strong> (7.40 mmol) in DMF (30 mL) wasadded under argon dry K2CO3 (10.73 mmol) and the correspondingalkyl halide (8.88 mmol). The mixture was stirred at room temperatureuntil thin layer chromatography (TLC) revealed that thestarting materialwas consumed. The solvent was evaporated underreduced pressure and the residue was purified on silica gel columnchromatography (CH2Cl2/MeOH, 0-10%) to provide compounds1-3 whereas compound 4 was isolated after precipitation in waterand filtration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1. 135635g (5.5mmol) of diethylenetriamine pentaacetic acid dianhydride (dtpaa), 2.334mL of triethylamine (16.5mmol), anhydrous DMF (50mL), <strong>[73-24-5]adenine</strong> (A) 0.7432g (5.5mmol), In a three-necked round bottom flask. Stir at a constant temperature of 100 C, and condense and reflux for 24 h. Further, 0.6105 g (5.5 mmol) of cytosine was added to the above reaction solution, and the mixture was rapidly stirred at a constant temperature of 100 C, and condensed and refluxed for 24 hours. After completion of the reaction, the mixture was allowed to stand. After cooling to room temperature, the solvent was evaporated to give a white solid material, which was filtered, filtered, and then washed three times with acetonitrile and anhydrous diethyl ether (3×10 mL). After drying at 50 C, <strong>[73-24-5]adenine</strong>-diethylenetriamine pentaacetic acid-cytosine (dtpa-AC) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In N,N-dimethyl-formamide; at 100℃; for 24h; | Take diethylene triamine pentaacetic acid dianhydride (dtpaa) 1.9635g (5.5mmol),2.334 mL of triethylamine (16.5 mmol),Anhydrous DMF (50 mL),Adenine (A) 1.4864g (11mmol),In a three-necked round bottom flask.Stir at a constant temperature of 100 C, and condense and reflux for 24 h.After completion of the reaction, the mixture was allowed to stand. After cooling to room temperature, the solvent was evaporated to give a white solid material, which was filtered, filtered, and then washed three times with acetonitrile and anhydrous diethyl ether (3×10 mL).Drying at 50 C gives diethylene triamine pentaacetic acid - bis (<strong>[73-24-5]adenine</strong>) (dtpa-2A). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | [0102] 3-(<strong>[73-24-5]adenine</strong>-9-yl) propylamine was synthesized by modifying a procedure previously described by Spijker et al.26 Adenine (7.832 g, 57.96 mmol) and sodium hydride (1 .55 g, 64.5 mmol) were introduced in a round bottom flask and subjected to 3 argon-vacuum cycles. 300 ml_ of anhydrous dimethyl formamide (DMF) were added and the suspension was stirred for 1 hour until no more hydrogen gas was produced. Then, a solution of 3-(Boc-amino) propyl bromide (17.91 g, 75.19 mmol) in 90 ml_ of anhydrous DMF was added drop- by-drop. After 2 days of reaction at room temperature, the solvent was evaporated in vacuo and the resulting solid was redissolved by a mixture of 700 mL of DCM and 300 ml_ of water. The organic fraction was washed 3 times with 300 mL of water and was then dried on a rotary evaporator. The resulting oil was dissolved in 250 mL of a 2 M hydrochloric acid solution in methanol to allow the deprotection of the primary amine. As the reaction proceeded, the desired product precipitated from the solution. The product was centrifuged at 5000 x g for 20 minutes (Thermo Scientific, Heraeus Megafuge 16R, TX-400 x 400 mL Swinging Bucket Rotor). The resulting pellets were resuspended 3 times in methanol and centrifuged in the same manner. The product was dried overnight in vacuo at 40 C. A white solid was obtained (5.76 g, 52 %). 1H NMR (D2O): delta/ppm 8.44 (s, 1 H), 8.37 (s, 1 H), 4.44 (t, 2H), 3.06 (t, 2H), 2.29 (q, 2H). 3C NMR (D2O): delta/ppm 149.73, 148.63, 141 .70, 144.34, 1 18.1 1 , 41 .50, 36.68, 27.25. The carbon and proton assignation and the integrals can be found in Supplementary Figure S12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46.18% | With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 95℃; for 9h;Large scale; | Add 24,000 kg of N,N-dimethylformamide to a 500 L glass-lined reaction tank.Turn on the agitation,Add <strong>[73-24-5]adenine</strong> 15.48kg, anhydrous potassium carbonate 26.40kg and[(2-chloroethoxy)methyl]phosphonic acid di(pivaloyloxymethyl) ester 39.392 kg,Warm up to 90 ~ 95 C,Insulation reaction for 9h,The TLC method monitors the reaction endpoint. The reaction is completed,Stir and cool to 20 ~ 30 C,1.1 kg of diatomaceous earth was added and stirred for 1 h. The filtrate was centrifuged, and the filtrate was concentrated under reduced pressure. After the concentration was completed, 35.2 kg of saturated brine was added to the reaction tank, and the residue was dissolved by stirring. The mixture was extracted with dichloromethane for 4 times, each time using 81.0 kg of dichloromethane, and the dichloromethane layer was combined, and anhydrous sodium sulfate (22.0 kg) was added. Dry, filter, and concentrate the filtrate under reduced pressure. After concentration, 336.0 kg of ethyl acetate was added to the reaction tank.Stirring to reflux, stirring at reflux for 1 h, filtering while hot, cooling the filtrate to 20-30 C, stirring and crystallization for 3 h, centrifuging and filtering, collecting the filter cake.Drying at 60 ± 5 C for 10 h gave 22.49 kg of a white solid, That is, adefovir dipivoxil. Yield: 46.18%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol; water;Heating; | General procedure: Compounds I and II were prepared by mixing hot methanol-water (1:1 v/v) solutions (total volume 8 ml) of <strong>[73-24-5]adenine</strong> (0.2 mmol and 0.4 mmol for I and II, respectively) with salicylic acid (0.2 mmol). The mixtures were stirred on awater bath until clear solutions were obtained and then cooledto room temperature after filtration. Colourless crystals (68%yield for I and 64% yield for II) were collected from therespective mother liquors after approximately 4-5 d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In methanol; water;Heating; | General procedure: Compounds I and II were prepared by mixing hot methanol-water (1:1 v/v) solutions (total volume 8 ml) of <strong>[73-24-5]adenine</strong> (0.2 mmol and 0.4 mmol for I and II, respectively) with salicylic acid (0.2 mmol). The mixtures were stirred on awater bath until clear solutions were obtained and then cooledto room temperature after filtration. Colourless crystals (68%yield for I and 64% yield for II) were collected from therespective mother liquors after approximately 4-5 d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With pyridine; at 20 - 100℃; for 18.5h; | This compound was synthesized via anadapted literature reported procedure [S17]. Chlorocarbonylazobenzene 26 (636 mg, 2.6 mmol,1.1 equiv) was added dropwise over 30 min to a stirred suspension of <strong>[73-24-5]adenine</strong> 27 (324 mg, 2.4 mmol,1.0 equiv) in dry pyridine and stirring was continued for two hours at 100 C. The mixture was cooledto room temperature and stirred for additional 16 hours. The reaction was quenched with methanoland the solvents were removed under reduced pressure. Purification by column chromatographyusing CH2Cl2 as the eluent afforded the desired product as orange solid (684 mg, 2.0 mmol, 83%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.3% | With bromine; In water; at 20℃; for 48h; | To a mixture of adenine (2.2 g, 16.3 mmol) in water (200 ml) was added bromine (6.0 ml, 17.7 mmol) dropwise at r. t. The resulting mixture was then stirred for 2 days at r. t. The solvent and volatiles were removed in vacuo. The residue was washed with water (15 mL x2) and EA (15 mL x2) to give 8-bromo-9H-purin-6-ylamine (2.1 g, yield: 60.3%) as a yellow solid.1H NMR (400 MHz, DMSO-r/d): d = 8.90 (br, 2H), 8.46 (s, 1H). MS: m/z 213.9 (M+H+). |
Tags: 73-24-5 synthesis path| 73-24-5 SDS| 73-24-5 COA| 73-24-5 purity| 73-24-5 application| 73-24-5 NMR| 73-24-5 COA| 73-24-5 structure
A114669[ 2922-28-3 ]
7H-Purin-6-amine hydrochloride
Reason: Free-salt
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P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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