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CAS No. : | 608-34-4 | MDL No. : | MFCD00038014 |
Formula : | C5H6N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VPLZGVOSFFCKFC-UHFFFAOYSA-N |
M.W : | 126.11 | Pubchem ID : | 79066 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.2 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 32.58 |
TPSA : | 54.86 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) : | -7.63 cm/s |
Log Po/w (iLOGP) : | 1.01 |
Log Po/w (XLOGP3) : | -0.79 |
Log Po/w (WLOGP) : | -0.93 |
Log Po/w (MLOGP) : | -0.8 |
Log Po/w (SILICOS-IT) : | 0.63 |
Consensus Log Po/w : | -0.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.62 |
Solubility : | 30.4 mg/ml ; 0.241 mol/l |
Class : | Very soluble |
Log S (Ali) : | 0.12 |
Solubility : | 165.0 mg/ml ; 1.31 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | -0.99 |
Solubility : | 13.0 mg/ml ; 0.103 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.44 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
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 |
---|---|---|
C. 20 g of 3-methyluracil-5-carboxylic acid was decarboxylated at 260 C. to give a quantitative yield of 3-methyluracil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 25% 2: 72% | With oxygen; ozone In acetic acid for 0.1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 8-quinolinol; potassium carbonate;copper(l) iodide; In dimethyl sulfoxide; at 130℃; | Example 38 5-chloro-N-((1-(4-(3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (49) A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 (66 mg, 0.15 mmol), <strong>[608-34-4]3-methyluracil</strong> (60 mg, 0.48 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (60 mg, 0.43 mmol) in DMSO (1 mL) was degassed with Ar before being charged with CuI (15 mg, 0.079 mmol). The mixture in a sealed tube was heated at 130 C. overnight. The mixture was then purified by HPLC to give the titled compound (15 mg). MS 442.2 and 444.2 (M+H, Cl pattern). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In water; | (b) Preparation of 6-amino-1-(2-hydroxypyropyl)-3-methyl-2,4- -(1H, 3H)-pyrimidinedione IV To 120 ml of 5 N NaOH (0.6 mol) was added 106.5 g (0.58 mol) of 6-amino-1-(2-hydroxypropyl)-2,4-(1H, 3H)-pyrimidinedione (III) in small portions. The solution was stirred and 67 ml (0.7 mol) of dimethylsulphate was added dropwise and the temperature was not allowed to go above 40 C. After all the dimethylsulphate was added, the received suspension was heated to 60 C. and neutralized to pH 6. After cooling white crystals were filtered off and recrystallized from 100 ml of water. Yield 79 g (IV) NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | EXAMPLE 1; (6aR,9aS)-5,6a,7,8,9,9a-hexahydro-5-methyl-2-((4-Pyridin-2yl)-benzyl)- cyclopent[4,5]imidazo[l,2-a]pyrrolo[4,3-e]pyrimidin-4(2H)-one; l) 2-((lR,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one; [0080] 3-Methyluracil (12.6 mg, 0.1 mmol) was dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) was added. The mixture was stirred at room temperature for two minutes, then (IR, 2R)-(-)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) was added, followed by DBU (5IuL, 3.4 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+. | |
76% | Step 1: 2-((lR,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one[0010] 3-Methyluracil (12.6 mg, 0.1 mmol) is dissolved in 0.5 mL of DMF, and then BOP (71 mg, 0.16 mmol) is added. The mixture is stirred at room temperature for two minutes, and then (1R, 2R)-(-)-2-hydroxycyclopentylamine hydrochloride salt (22 mg, 0.16 mmol) is added, followed by DBU (51uL, 3.4 mmol). The reaction mixture is stirred at room temperature overnight, and then purified by a semi-preparative HPLC to give pure product (16 mg, yield 76%). MS (ESI) m/z 210.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl-formamide; at 18 - 25℃; | Example 1:6-(4-(6-fluoropyridin-2-yl)benzyl)-l-isobutyI-3-methyl-7-(phenyIamino)-lH- pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione 1) l-isobutyl-3-methylpyrimidine-2,4(lH,3H)-dione[0081] A suspension of 3-Methyluracil (3.0 mg, 23.8 mmol), isobutyl iodide (7 mL, 60 mmol) and cesium carbonate (11.6 g, 35.7 mmol) in DMF (30 mL) is stirred at room temperature over a weekend. Solvent is removed under vacuum. The residue is treated with water, and then extracted with dichloromethane four times. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and then filtered through a short silica gel column. The filtrate is concentrated to dryness to give product as off white solids, which is used for the next reaction without further purification. MS (ESI) m/z 183.1 [M+H]+. | |
With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; | A suspension of 3-Methyluracil (3.0 g, 23.8 mmol), isobutyl iodide (7 mL, 60 mmol) and cesium carbonate (11.6 g, 35.7 mmol) in DMF (30 mL) is stirred at room temperature over a weekend. Solvent is removed under vacuum. The residue is treated with water, and then extracted with dichloromethane four times. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and then filtered through a short silica gel column. The filtrate is concentrated to dryness to give product as off white solids, which is used in the next step without further purification. MS (ESI) m/z 183.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; dmap; triethylamine; In toluene; at 90℃; for 3h; | General procedure: Compounds 1-15 were synthesized according to Scheme 1. The appropriately substitutedcarboxylic acid (0.5 mmol) was dissolved in dry CH2Cl2 (5 mL). Oxalyl chloride (0.6 mmol, 0.05 mL)and DMF (0.01 mL) were added, and the reaction mixture was stirred at 0 C for 1 h. The solventwas evaporated under reduced pressure, keeping the temperature below 30 C. The crude residuewas redissolved with anhydrous acetone (5 mL) and then dropwise added into a stirred and ice-coldsolution of NaN3 (1.0 mmol, 33 mg) in H2O (1 mL). The resulting mixture was stirred at 0 C for30 min, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrousNa2SO4, and concentrated under reduced pressure. The residue was then dissolved in toluene (15 mL),and refluxed for 2 h. The reaction solution was cooled to room temperature, and dropwise added toa solution of the corresponding uracil derivatives (0.5 mmol) in dry pyridine (0.5 mL). After beingstirred at 90 C for 3 h, the mixture was cooled and evaporated. The crude was purified by flashchromatography on silica gel to afford compounds 1-15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium tert-butylate; In N,N-dimethyl-formamide; at 0 - 20℃; under 760.051 Torr;Inert atmosphere; | In a 50 niL round-bottomed flask, potassium 2-methylpropan-2-olate (445 mg, 3.96 mmol, Eq: 1.00) and 3-methylpyrimidine-2,4(lH,3H)-dione (0.5 g, 3.96 mmol, Eq: 1.00) were combined with DMF (5.0 ml) to give a light brown suspension at 0C under nitrogen. 2-Chloro- l-fluoro-4-nitrobenzene (696 mg, 3.96 mmol, Eq: 1.00) was added. The reaction was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, the compound was isolated by column chromatography (Hexanes / EtOAc = 50/50) to give the product 0.79 g (71%). MH+ 282.0 |
Tags: 608-34-4 synthesis path| 608-34-4 SDS| 608-34-4 COA| 608-34-4 purity| 608-34-4 application| 608-34-4 NMR| 608-34-4 COA| 608-34-4 structure
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