There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
Inaccessible (Haz class 6.1), International | USD 150+ |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 100+ |
Accessible (Haz class 3, 4, 5 or 8), International | USD 200+ |
Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 51953-17-4 | MDL No. : | MFCD00006664 |
Formula : | C4H4N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DNCYBUMDUBHIJZ-UHFFFAOYSA-N |
M.W : | 96.09 | Pubchem ID : | 20695 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 24.86 |
TPSA : | 45.75 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) : | -7.39 cm/s |
Log Po/w (iLOGP) : | 0.47 |
Log Po/w (XLOGP3) : | -0.71 |
Log Po/w (WLOGP) : | -0.23 |
Log Po/w (MLOGP) : | -0.68 |
Log Po/w (SILICOS-IT) : | 1.24 |
Consensus Log Po/w : | 0.02 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.62 |
Solubility : | 22.9 mg/ml ; 0.238 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.22 |
Solubility : | 161.0 mg/ml ; 1.68 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -1.47 |
Solubility : | 3.23 mg/ml ; 0.0337 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.2 |
Signal Word: | Danger | Class: | 4.1 |
Precautionary Statements: | P210-P273-P243-P403 | UN#: | 1325 |
Hazard Statements: | H228 | 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 |
---|---|---|
36% | With diphosphorus pentasulfide In pyridine; water | Step a Preparation of 4-mercaptopyrimidine 4-Hydroxypyrimidine (1g) and phosphorus pentasulphide (2.32g) were stirred together in 15ml of pyridine and heated to reflux. After 3 hours at reflux the reaction mixture was allowed to cool, then 30 ml of water was added and the reaction mixture concentrated under reduced pressure. The concentrated mixture was extracted with ethyl acetate (3*30ml) and the combined organic extracts were washed with water, dried over anhydrous MgSO4, filtered and the solvent evaporated under reduced pressure to yield a yellow solid (0.42 g, 36percent). The product of this reaction was used in the next preparative step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform lactim-lactam equilibrium, variation of solvents; | ||
In gaseous matrix ΔRGo, tests in solvents of different polarity; | ||
Irradiation; phototautomerism; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In solid matrix at -267.2 - -266.2℃; Irradiation; photochemistry of other matrix isolated 4(3H)-pyrimidinones; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 25% 2: 19% | With N,N,N',N'-tetramethylguanidine In N,N-dimethyl-formamide for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 16% 2: 21% | With pyridine In ethanol for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform lactim-lactam equilibrium, variation of solvents; | ||
In gaseous matrix ΔRGo, tests in solvents of different polarity; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19% 2: 2% | With tin(IV) chloride In acetonitrile for 12h; Ambient temperature; further reagents: 1.) (Me3Si)2NH, 2.) SnCl4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With Agrobacterium sp. DSM 6136 for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
E(Tautomerie); | ||
Rk. in 1.5 n NaOH mit Jod bei 50-60grad/30 ' -> 4-Hydroxy-5-jod-pyrimidin; | ||
Rk. m. 1. POCl3, 2. Me., 3. Na-Methylat, 4. CO2, 5. Hydrazinhydrat zu 4-Hydrazino-pyrimidin; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
/BRN= 31430/, NaOH; | ||
4-Chlor-pyrimidin-hydrochlorid, Thioharnstoff; | ||
2-Thio-uracil, Desulfurier. m. Raney-Ni; |
(yield)70percent; | ||
... 2, characterized by the fact that the respective persilylated pyrimidine derivatives are converted with metallo-organic compounds such as butyl lithium or sodium amide, converting compound III formed in the reaction mixture directly with halogenosis II. 6-methylene substituted nucleosides of 4-hydroxypyrimidine, 4-aminopyrimidine, 2-amino-4-hydroxypyrimidine and 2,4-diaminopyrimidine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 55℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With trichlorophosphate at 100℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With di-isopropyl azodicarboxylate; triphenylphosphine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium fluoride; sodium iodide In N,N-dimethyl-formamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 49.5% 2: 19.92% | With potassium carbonate; sodium iodide In acetonitrile for 90h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With sodium; In ethanol; for 3.0h;Heating / reflux; | To a pre-formed solution of sodium (1.70 g, 73.9 mmol) in absolute ethanol(300ml) was added 1,3,5-triazine (6.0 g, 74.1 mmol) and diethylmalonate (11.3 ml, 74.1 mmol). The reaction mixture was heated to reflux. After heating for 3h, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford a residue. The residue was dissolved in water (300 ml), then cooled to 5C and acidified by addition of hydrochloric acid (6 ml). The mixture was aged for 48 hours at 5C and filtered. The resultant solid was washed with water, before being dried under reduced pressure to give the title compound as a beige solid (3.0g, 24%). 1H NMR (d6-DMSO, 400 MHz) 8.47 (s, IH), 8.37 (d, s, IH), 4.22 (q, J = 7.2 Hz, 2H), 1.26 (t, J = 7.2 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | With potassium carbonate In ethanol for 100h; Heating / reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 18 - 26℃; for 0.5h; | 4 5(R)-Hydroxymethyl-3-(4-(4-(5-cyanopyrid-2-yl)piperazin-1-yl)-3-fluorophenyl)-oxazolidin-2-one (397 mg, 1 mM), 4-hydroxypyrimidine (106 mg, 1.1 mM) and triphenylphosphine (327 mg, 1.25 mM), were suspended with stirring in dry tetrahydrofuran (10 ml). Diisopropylazodicarboxylate (242 mg, 1.2 mM) was added dropwise by syringe, and the mixture stirred at ambient temperature for 30 minutes. The reaction mixture was evaporated to dryness, dissolved in ethyl acetate / isohexane (3:1), and applied to a 20 g silica Mega Bond Elut column, eluting with a gradient increasing in polarity from 3:1 ethyl acetate inisohexane to pure ethyl acetate. Relevant fractions were combined and evaporated to give the title compound (240 mg). MS (ESP): 476 (MH+) for C24H22FN7O3. 1H-NMR (300MHz,DMSO) : δ: 3.03 (t, 4H); 3.79 (t, 4H); 3.89 (dd, 1H); 4.17 (t, 1H); 4.56 (dd, 1H); 4.61 (dd, 1H); 5.06 (m, 1H); 6.96 (overlapping m, 2H); 7.08 (t, 1H); 7.20 (dd, 1H); 7.51 (dd, 1H); 7.86 (dd, 1H); 8.50 (d, 1H); 8.50 (d, 1H); 8.79 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With bromine; acetic acid In dichloromethane | 242.A 5-Bromo-pyrimidin-4-ol Example 242A 5-Bromo-pyrimidin-4-ol The Pyrimidin-4-ol (366 mg, 3.8 mmol) and AcOH were cooled to 0° C. Br2 (0.27 ml) was added slowly via syringe. The mixture was stirred at room temperature for 3 hours. The AcOH was removed under pressure. The residue was dissolved in CH2Cl2, washed with saturated NaHCO3, brine, and dried over MgSO4. The solvent was removed and the product was purified by flash column chromatography to afforded the desired product (605 mg, 91%). MS (ESI) m/e 175 (M+1)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 8.23 (br. s., 1H) 8.33 (br. s., 1H) 13.08 (br. s., 1H). |
91% | With bromine In acetic acid at 0 - 20℃; for 3h; | 242.A 5-Bromo-pyrimidin-4-ol Example 242A 5-Bromo-pyrimidin-4-ol The Pyrimidin-4-ol (366 mg, 3.8 mmol) and AcOH were cooled to 0° C. Br2 (0.27 ml) was added slowly via syringe. The mixture was stirred at room temperature for 3 hours. The AcOH was removed under pressure. The residue was dissolved in CH2Cl2, washed with saturated NaHCO3, brine, and dried over MgSO4. The solvent was removed and the product was purified by flash column chromatography to afforded the desired product (605 mg, 91%). MS (ESI) m/e 175 (M+1)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 8.23 (br. s., 1H) 8.33 (br. s., 1H) 13.08 (br. s., 1H). |
72% | With bromine; acetic acid at 4 - 20℃; for 3h; | 11 EXAMPLE 11: 5-bromopyrimidin-4-ol14To a stirred solution pyridine -4-ol (500mg, 5.208mmol) in acetic acid maintained at 4-6°C, bromine was slowly added. The cooling mixture was removed and stirred at RT for 3h. TLC was checked. Reaction mixture was concentrated and the residue was washed with ether to get the desired product 14, as brown solid, 650mg (Yield- 72%). The product was confirmed by 1HNMR and MS spectrum analysis. 1H NMR (400 MHz, CDC13) δ: 9.45-9.7 (bs, 3H), 8.29 (s, 1H), 8.23 (s, 1H); MS- 174 (M+l). |
50% | With bromine; acetic acid at 20℃; | Step 1 - Synthesis of 5-bromopyrimidin-4-ol (1-111 ) To a solution of pyrimidin-4-ol (1-110) (50 g, 0.52 mol) in AcOH (800 mL) was added in a dropwise manner a solution of Br2 (88 g, 0.55 mol) in AcOH (100 mL) over a period of 30 min at room temperature. Then the resulting mixture was stirred at room temperature overnight. The reaction mixture was filtered, and the cake was washed with petroleum ether (200 mL), and neutralized with saturated aq. NaHC03 (500 mL) carefully. The suspension was filtered, the cake was washed with H20 (100 mL), dried under high vacuum to give 5-bromopyrimidin-4-ol (I-111) (45 g, 50%) as a pale white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32 N-(2-Iodo-4-(1-Methylethyl)Phenyl)-N-Ethyl-4-Chloro-6-Methyl-2-Pyrimidinamine EXAMPLE 32 N-(2-Iodo-4-(1-Methylethyl)Phenyl)-N-Ethyl-4-Chloro-6-Methyl-2-Pyrimidinamine Guanidine 39.5 mmoles crude, obtained by treatment of the corresponding guanidinium salt with K2 CO3, 15 mL (118 mmoles) ethyl acetoacetate and 2.0 g (14.47 mmoles) K2 CO3 were heated to reflux in 120 mL absolute ethanol for 100 hr. Then the solvent was stripped in vacuo and the residue was chromatographed on silica gel using 40% EtOAc/hexanes as eluent to give 4 g product, a 27% yield for the three steps. The 4-hydroxypyrimidine obtained from the above reaction (2.47 g, 6.69 mmoles) was dissolved into 20 mL POCl3 and stirred at 25° C. for 4 hr. The reaction mixture was poured into ice, stirred for 30 min, and extracted with 100 mL EtOAc. The EtOAc extract was washed with brine, dried and stripped in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With diphosphorus pentasulfide; In pyridine; water; | Step a Preparation of 4-mercaptopyrimidine 4-Hydroxypyrimidine (1g) and phosphorus pentasulphide (2.32g) were stirred together in 15ml of pyridine and heated to reflux. After 3 hours at reflux the reaction mixture was allowed to cool, then 30 ml of water was added and the reaction mixture concentrated under reduced pressure. The concentrated mixture was extracted with ethyl acetate (3*30ml) and the combined organic extracts were washed with water, dried over anhydrous MgSO4, filtered and the solvent evaporated under reduced pressure to yield a yellow solid (0.42 g, 36%). The product of this reaction was used in the next preparative step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h; | II.7 EXAMPLE 7:; 2-terf-Butvl-4-cvclobutvl-6-{4-r3-(pvrimidin-4-vloxv)-propyll-piperazin-1-vl)-pvrimidine; 0.2 g of 4-hydroxy-pyrimidine (2.08 mmol) were dissolved in 15 ml of dimethylform-amide. After addition of 0.58 g of potassium carbonate (4.16 mmol) and 0.73 g of 2-tert-/jufy/-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (2.08 mmol), the mixture was stirred at 90°C for 3 h. The dimethylformamide was removed under reduced pressure and the resulting residue was partitioned between 40 ml of ethyl acetate and 20 ml of water. The aqueous phase was re-extracted with ethyl acetate, the organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel with ethyl acetate-methanol (2-10%). Fractions containing the product were combined. The solvent was evaporated. The product crystallized upon standing (yield: 0.2 g).MS (ESI) m/z: 411.5 [M+H]+1H-NMR (DMSO): 5 [ppm] 8.8 (s, 1H), 8.5 (d, 1H), 6.9 (d, 1H), 6.4 (s, 1H), 4.4 (m, 2H), 3.6 (m, br, 4H), 3.3-3.45 (m, 2H), 2.4 (m, 5H), 2.1-2.3 (m, 4H), 1.95 (m, 3H), 1.85 (m, 1H), 1.3 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate In <i>N</i>-methyl-acetamide; toluene | R.17.4 4-Chloro-5-cyano-6-difluoromethylpyrimidine (Compound No. 1-17) (4) 4-Hydroxypyrimidine 0.3 g (1.75 mmol) prepared in the Reference Example 17(3) was suspended in toluene (5 ml), and to the suspension were added phosphorous oxychloride (0.5 ml) and dimethylformamide (one drop). The mixture was stirred at 80ØC for 1 hr, and then cooled. After removal of the insolubles by decantation, the toluene solution was concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 1: 1) to give 4-chloro-5-cyano-6-difluoromethylpyrimidine (0.2 g).1H-NMR(CDCl3) 6 6.72 (1H, t, J=53.1Hz), 9.23 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; trichlorophosphate | R.18.2 4-Chloro-5-cyano-6-methylpyrimidine (Compound No. 1-18) (2) 4-Hydroxypyrimidine 6.8 g (50.4 mmol) was suspended in phosphorous oxychloride (25 ml), and the suspension was stirred at 100ØC for 30 minutes. After cooling, the reaction mixture was concentrated and the residue was diluted with ethyl acetate, then washed with water. The ethyl acetate layer was dried and concentrated. The residue was dissolved in hexane and the insolubles were removed by filtration. The filtrate was concentrated to give 4-chloro-5-cyano-6-methylpyrimidine (2.7 g). 1H-NMR(CDCl3) δ 2.80 (3H, s), 9.00 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Pyrimidin-4-ol With sodium hydroxide; iodine In water at 80℃; Stage #2: With acetic acid In water | 243.1 EXAMPLE 243; Synthesis of 4-phenyl-N-(4-(5(pyridin-4-yl)pyrimidin-4-yloxy)phenyl)phthalazin-1-amine; Step 1. Preparation of 5-iodopyrimidin-4-ol; The title compound was prepared following the literature reference: Chem. Pharm. Bull. 1986, 34, 2719-2714. As described therein, to a light yellow solution of pyrimidin-4-ol (10.0 g, 104 mmol) in sodium hydride 6.0 M (23.1 ml, 139 mmol) and water (77 mL) was added iodine (26.4 g, 104 mmol). The mixture was heated to 80° C., with an air-cooled condenser, and became quite thick after 5 min. After 30 min, the mixture was easy to stir and red/purplish in color. The reaction was heated overnight, then cooled and neutralized by a small amount of AcOH. The precipitate was collected by filtration, rinsed with 100 mL water, and was dried in vacuo to give 5-iodopyrimidin-4-ol as a tan solid. MS m/z=223 [M+H]+. Calc'd for C4H3IN2O: 222.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 18% | In ethanol; water addn. of 4 equiv. of pyrimidine-derivative to RhCl3 soln. (in 30% aq. EtOH), refluxing for 1 h; filtration, drying (over CaO), concn. of filtrate, chromy. (QAE C-25 Sephadex in Na(+) form, 0.1 M NaCl), evapn., extn. into EtOH, evapn.; elem.anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In water; acetonitrile calcd. amts. of compds. dissolved in MeCN, reacted in sealed glass tubeat 100°C for 48 h; slow cooling to 20°C (1°C/h); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triethylamine In water dissolved, slowly evapd. at room temp. for 2 d; elem. anal.; | |
50% | In ammonia aq. NH3; dissolved, slowly evapd. at room temp. for 2 d; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In ammonia aq. NH3; dissolved, slowly evapd. at room temp. for 2 d; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In neat (no solvent, solid phase) ZnO and 4-hydroxypyrimidine ground, heated at 140°C for 2 h underN2; suspended in acetone, stirred at room temp. for 2 h, washed (acetone), dried (air); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With NaOH In water an aq. soln. contg. 4-hydroxypyrimidine and NaOH added dropwise into an aq. soln. of Ni salt, stirred at room temp. for 2 h; washed with EtOH and Et2O, dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20 - 75℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; acetone for 1h; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile at 20℃; for 24h; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With trichlorophosphate at 110℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 25℃; | General synthesis of the Cu compounds General procedure: 1 mmol of Cu(CH3COO)2·H2O in 10 mL of water was added dropwise to a mixed-ligand solution of 2,6-pyridinedicarboxylic acid (1 mmol) and the appropriate pyrimidine ligand (1 mmol) in 20 mL of water with stirring at room temperature. The solution was filtered and left standing at ambient temperature. After a few days blue crystals appeared. These were washed and dried at room temperature. Crystals for X-ray diffraction were used directly from the mother liquid. Yield ca. 75-85%. Elemental Anal. Calc. for C11H15CuN3O9 (1): C, 33.3; H, 3.8; N, 10.6. Found: C, 33.4; H, 3.9; N, 10.6%; for C11H9CuN5O7 (2): C, 34.2; H, 2.3; N, 18.1. Found: C, 34.1; H, 2.2; N, 18.1%; for C11H11ClCuN4O6 (3): C, 33.5; H, 2.8; N, 14.2. Found: C, 33.5; H, 2.7; N, 14.3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium carbonate; sodium iodide In acetone for 24h; Reflux; | 22 General experimental procedure for the preparation of compounds 5a-h General procedure: A mixture of 3,4-dihydroquinazolin-4-one (4, 0.5 mmol), sodium iodide (0.05 mmol), potassium carbonate (2.5mmol) and an appropriate alkylating agent (0.5 mmol) in acetone (5 mL) was heated under reflux for 24 h. The resultant mixture was diluted with ethyl acetate (10 mL), washed with brine (10 mL) and organic phase was dried with sodium sulfate. Crude products were purified by column chromatography (hexane-ethyl acetate 8:2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With tetrakis(triphenylphosphine) palladium(0) at 100℃; for 12h; Inert atmosphere; Glovebox; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: Pyrimidin-4-ol With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 20℃; for 2h; Inert atmosphere; Stage #2: phenyl carbamate With tris-(dibenzylideneacetone)dipalladium(0); 2-(3-(2-(diphenylphosphino)phenyl)-1H-pyrazol-1-yl)-4,6-dimethoxy1,3,5-triazine; caesium carbonate In 1,4-dioxane; water at 100℃; for 4h; Inert atmosphere; | 7.6 General procedures coupling reactions General procedure: To an oven dried flat-bottomed flask, which was equipped with a magnetic stir bar, was charged with heteroarenol (1mmol), PyBroP (1.50mmol), triethyl amine (2.0mmol)in dried 1,4-dioxane (5.0mL).The reaction was sparged with nitrogen for 15min, stirred and heated to rt for 2h. The reaction was then recharged with urea (1.00mol), Cs2CO3 (1.4mmol), ligand L (5mol%), Pd2(dba)3(3.3mol%), water (1mL). The mixture was stirred at 100°C for 4h. After completion of the reaction, mixture was cooled to room temperature and filtered through a pad of Celite eluting with ethyl acetate. The filtrate was concentrated and purification of the residue by silica gel column chromatography gave the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With palladium diacetate; acetic acid In acetonitrile at 120℃; for 24h; Sealed tube; regioselective reaction; | 13 4.2. Experimental procedure General procedure: Unless otherwise stated, the procedure was as follows. To a 1-dram (4 mL) vial equipped with a magnetic stir bar were added Pd(OAc)2 (4.4 mg, 0.02 mmol), alkene (0.2 mmol), acetic acid (6.0 mg, 0.1 mmol), nucleophile (0.3 mmol), and MeCN (0.1 mL). The vial was sealed with an unpunctured TFE septum-covered screw cap, and placed in a heating block that was pre-heated to 120 °C. After the designated reaction time, the dark black reaction was purified either by flash column chromatography only or by flash column chromatography followed by an aqueous workup to produce the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triphenylphosphine; bis(dibenzylideneacetone)-palladium(0); 3-chlorobenzoate In 1,4-dioxane at 140℃; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74 % ee | With C24H18F2N2O2; N-ethyl-N,N-diisopropylamine; copper(l) chloride In chloroform; 2,2,2-trifluoroethanol at -40℃; for 60h; Inert atmosphere; Schlenk technique; Overall yield = 79 %; Overall yield = 76.8 mg; enantioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40 mg | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 15h; | 35 Example 35. Preparation of (S)-N-(7-amiiio-2-oxo-l-(6-oxopyrimidin-l(6H)-yl)heptan-3- yl)cyclopentanecarboxamide (39) [0362] To 1.2 (150 mg, 357.7 μιτιο, 1 equivalent) in DMF (2 mL) was added K2C03 (148.31 mg, 1.07 mmol, 3 and 4-hydoxylpyrimidine (34.37 mg, 357.7 μιτιο, 1 equivalent). The mixture was stirred at 25 °C for 15 hours. The residue was purified by semi-preparative scale HPLC (TFA condition) to give 39.1 (40 mg, 92.05 μιηο); LCMS [M + H]: 435; RT = 0.76 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With silver carbonate In N,N-dimethyl-formamide at 25℃; for 15h; | 36 Example 36. Preparation of (S)-N-(7-amino-2-oxo-l-(4-oxopyrimidin-l(4H)-yl)heptan-3- yl)cyclopentanecarboxamide (40) [0364] To 1.2 (100 mg, 238.46 μηιο, 1 equivalent) in DMF (3 mL) was added Ag2C03 (197.27 mg, 715.38 μηιο, 32.45 μΤ, 3.00 equivalent) and 4-hydroxypynmidine (22.91 mg, 238.46 μιηο, 1 equivalent). The mixture was stirred at 25 °C for 15 hours. The residue was purified by semi-preparative scale HPLC (TFA condition) to give 40.1 (30 mg, 69.04 μηιο, 29% yield) as a white solid; LCMS [M + H]: 435; RT=0.74 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
700 mg | With phosphorus(V) oxybromide at 100℃; for 4h; | Preparation of 4-(trimethylstannyl)pyrimidine A mixture of pyrimidin-4-ol (1.0 g, 10.4 mmol) with POBr3 (3.3 g, 11.5 mmol) was stirred at100°C for 4 hours. Cooled to 30°C and poured into ice-water (20 g), aqueous NaHCO3 wasadded until pH=7 and extracted with dichloromethane (15 mL x 3). The combined organicphases were washed with water, dried over Na2SO4, filtered and concentrated under vacuum to afford 4-bromopyrimidine (700 mg). 1H NMR (CDCI3 400 MHz): 68.97 (s, 1H), 8.52 (d, i = 5.2 Hz, 1H), 7.57 (d, i = 5.6 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 300 - 900℃; Inert atmosphere; Pyrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 23℃; Inert atmosphere; | ||
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With trichlorophosphate at 25℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | With sodium methylate In methanol at 21 - 24℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 150℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In methanol for 16h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane | 1 Example 1: Preparation of compound III-1 In a 250 ml two-necked round-bottom flask, add 2.4 g of 4-hydroxypyrimidine I, 4.4 g of 4-propargyloxybenzoic acid and 4.8 g of 1-ethyl-(3-dimethylaminopropyl) carbodiimide Amine hydrochloride (EDC). 100 mL of reaction solvent dichloromethane was added. After monitoring the reaction by TLC, the excess solvent was removed by concentration under reduced pressure, and the residue was purified by 100-200 mesh silica gel column chromatography to obtain compound III. The eluent was petroleum ether at 60-90 degrees Celsius: ethyl acetate, and the volume ratio was 6: 1. The product is 4.2 g of white powder, and the yield is 74%. |
Tags: 51953-17-4 synthesis path| 51953-17-4 SDS| 51953-17-4 COA| 51953-17-4 purity| 51953-17-4 application| 51953-17-4 NMR| 51953-17-4 COA| 51953-17-4 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
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.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :