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CAS No. : | 698-29-3 | MDL No. : | MFCD00084875 |
Formula : | C6H6N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YBPNIILOUYAGIF-UHFFFAOYSA-N |
M.W : | 134.14 | Pubchem ID : | 69682 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 36.12 |
TPSA : | 75.59 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) : | -6.74 cm/s |
Log Po/w (iLOGP) : | 1.21 |
Log Po/w (XLOGP3) : | 0.53 |
Log Po/w (WLOGP) : | 0.25 |
Log Po/w (MLOGP) : | -0.88 |
Log Po/w (SILICOS-IT) : | 0.57 |
Consensus Log Po/w : | 0.34 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.45 |
Solubility : | 4.76 mg/ml ; 0.0355 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.69 |
Solubility : | 2.75 mg/ml ; 0.0205 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.73 |
Solubility : | 2.47 mg/ml ; 0.0185 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.76 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | 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 |
---|---|---|
83% | With formic acid; nickel; In water; for 0.25h;Reflux; | (0273) To a solution of the compound of Reference Example 22 (50.0 g, 373 mmol) in formic acid (150 mL) were added water (65 mL) and Raney nickel (50 g). The mixture was heated under reflux for 15 minutes, cooled to room temperature, and filtrated through Celite, and then 28% ammonia water (220 mL) was added thereto under ice cooling. The mixture was stirred under ice cooling for 1 hour, and the precipitate was collected by filtration. The filter cake was washed with water (30 mL) and chloroform (30 mL×2), and dried in vacuo. Furthermore, the filtrate was extracted with chloroform (200 mL) nine times, and the combined organic layer was concentrated. The resulting concentrated residue and the above-obtained filter cake were mixed, chloroform (70 mL) was added thereto, the mixture was stirred at room temperature for 30 minutes, hexane (210 mL) was added dropwise thereto over 10 minutes, and the mixture was stirred at room temperature for additional 1 hour. The precipitate was collected by filtration, washed with hexane/chloroform (3/1, 28 mL), and dried in vacuo to give the title compound (42.6 g, 83%). 1H-NMR (400 MHz, CDCl3) delta: 2.57 (3H, s), 5.98 (1H, brs), 8.15 (1H, brs), 8.57 (1H, s), 9.86 (1H, s). |
83% | With formic acid; In water; for 0.25h;Reflux; | Compound of Reference Example 22 (50.0g, 373mmol) was added to the formic acid solution (150mL) and water (65mL) Raney nickel (50g). After heating to reflux for 15 min, cooled to room temperature, filtered through celite, under ice-cooling 28% aqueous ammonia (220 mL) was added, after stirring for 1 hour under ice-cooling, the precipitate was collected by filtration. The filtrate quality goods and washed with water (30 mL) and chloroform (30 mL × 2 times) followed by drying under reduced pressure. Further, the filtrate was extracted 9 times with chloroform (200 mL), the organic layer was concentrated. The combined quality goods braze obtained this concentrated residue before, chloroform (70 mL) was added, after stirring for 30 minutes at room temperature, hexane (210 mL) was added dropwise over 10 minutes, further stirred at room temperature for 1 hour. Thereafter, the precipitate was collected by filtration, washed with hexane / chloroform (3 / 1,28mL), the title compound was dried under reduced pressure (42.6g, 83%) was obtained. |
70% | With sulfuric acid; palladium 10% on activated carbon; hydrogen; In water; at 20℃; for 16h; | To a solution of 51 (700 mg, 5.2 rnrnoi) in water and H2S04 is added Pd/C (10 wt. %, 543 mg). After stirring at room temperature under hydrogen for 16 hours, the mixture is filtered through a. pad of? Celite and washed with water. The filtrate is treated with ammonium hydroxide, and the solid is collected by filtration and dried to give 52 (500 mg, 70%). (MS: [M±HI 1381) |
58.5% | 4-Amino-2-methylpyrimidine-5-carbonitrile (500 mg, 3.73 mmol) and 10% palladium on carbon (40.8 mg, 38.3 mumol) were combined in water (4 mL) and sulfuric acid (800 muL). The mixture was hydrogenated at room temperature and 30-50 psi for 75 minutes. The reaction mixture was filtered through Celite and washed with water. The filtrate was combined with the washes and treated with concentrated ammonium hydroxide. Solid precipitated out of solution, with heat given off. The mixture was chilled prior to collecting the solid by filtration. The filtered solid was washed with water and then dried under house vacuum to give 4-amino-2-methylpyrimidine-5-carbaldehyde. (Yield 299.2 mg, 2.18 mmol, 58.5%). | |
With formic acid; at 80℃; for 4h; | A solution of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong> 1a (3.04g, 30mmol) and raney nickel (3.0g) in formic acid (20mL) was stirred at 80C for 4h. After this, the reaction mixture was filtered and washed with 10mL formic acid. The filtrate and washings were collected together and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and eluted with ethyl acetate/petroleum ether (1:1, v/v) to give white solid 2a, which was used directly for the next step. Under this same condition, the intermediate compounds 2a and 2c were also prepared. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With ammonia; hydrogen; In methanol; at 60℃; under 30003 Torr; for 24h;Autoclave; | [0267j In an autoclave the mixture of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong> (16 g, 119 mmol), modified Raney nickel (wet weight 15 g), and saturated methanol solution of ammonia (200 mL) was heated to 60 C and stirred for 24 hrs at this temperature under 4 MPa of hydrogen pressure. The resulting reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (CH2C12/MeOH = 30/ii0/i) to afford 14.8 g of 5 -(aminomethyl)-2-methylpyrimidin-4-amine (90 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; hydrogen sulfide; triethylamine; In N-methyl-acetamide; | EXAMPLE 8 4-Amino-2-methyl-5-pyrimidinecarbothioamide Hydrogen sulfide is passed through a mixture of 4-amino-2-methyl-5-pyrimidinecarbonitrile (6.707 g., 0.050 m.), triethylamine (7.0 ml., 0.050 m.), dimethylformamide (25 ml.) and pyridine (100 ml.) with stirring for 3 hours at ambient temperature. The mixture is poured into ice water (500 ml.) and the cream-colored solid which separates is collected by filtration, washed with water, dried at 110 C./0.1 mm. The yield of product melting at 260 C. dec. (uncorr.) is 7.663 g. (91.1%). This material is recrystallized from dimethylformamide-water (Darco G-60) affording colorless crystals melting at 264 C. dec. (uncorr.) in a yield of 5.110 g. (60.8%). Analysis for: C6 H8 N4 S; Calculated: C, 42.83; H, 4.79; N, 33.32; S, 19.06; Found: C, 42.79; H, 4.83; N, 33.34; S, 19.19. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A solution of sodium ethoxide (1.15g, 50mmol), and acetamidine hydrochloride (4.7g, 50mmol) in ethanol solution (60mL) was stirred at room temperature for 1h. After this, the reaction mixture was filtered out affording filtrate. Then 2-(ethoxymethylene)malononitrile (6.1g, 50mmol) was added to the filtrate, and the mixture was stirred at room temperature for 3h. After this, the reaction mixture was filtered and washed with 10mL ethanol and dried to give the desired compound 4-amino-2-methylpyrimidine-5-carbonitrile 1a, which was used directly for the next step. Under the same condition, the intermediate compounds 1b and 1c were also prepared. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; formic acid;aluminum nickel; In water; hydrogen; | Method A 6-(2,6-Dichlorophenyl)-2-methylpyrido[2,3,-d]-pyrimidin-7-amine A mixture of 76.5 g of <strong>[698-29-3]4-amino-2-methylpyrimidine-5-carbonitrile</strong>, 380 ml of 97% formic acid, 380 ml of water, and 8 g of Raney nickel catalyst is treated in a Parr pressure apparatus with hydrogen gas at an initial pressure of 51 psi at room temperature for 2.75 hours. The catalyst is removed by filtration and the filtrate is treated with 47.5 ml of concentrated hydrochloric acid and evaporated at reduced pressure. The residue is dissolved in hot water, treated with charcoal and filtered. Neutralization of the filtrate with concentrated ammonium hydroxide precipitates the product which is then collected by filtration and washed with water. Recrystallization from ethanol gives 37.9 g of 4-amino-2-methylpyrimidine-5-carboxaldehyde, mp 191-192.5 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; In dimethyl sulfoxide; | EXAMPLE 5 4-Amino-2-methyl-5-pyrimidinecarboxamidoxime A solution of hydroxylamine base, prepared from hydroxylamine hydrochloride (7.296 g., 0.105 mole) and potassium t-butoxide (11.783 g., 0.105 mole) in dimethyl sulfoxide (200 ml.) in a manner similar to that of Example 1, is allowed to react with <strong>[698-29-3]4-amino-2-methyl-5-pyrimidine carbonitrile</strong> (13.414 g., 0.100 mole). After addition of dimethyl sulfoxide (50 ml.), the mixture is heated at 40+-1 C. for 92 hours. The solid which separates is collected by filtration, successively washed with methanol (1*50 ml.) and water (3*50 ml.) then dried at 110/0.1 mm. The yield of colorless crystals melting at 263 C. dec. (uncorr.) is 10.059 g. (60.2%). A second crop is obtained by concentrating the combined filtrates in vacuo to give a white solid. This material is washed with water, dried at 110 C./0.1 mm. The yield of colorless crystals melting at 256 C. dec. (uncorr.) is 6.300 g. (37.6%). The total yield of crude product is 16.359 g. (97.8%). The combined fractions are recrystallized from 2-methoxyethanol (Darco G-60) affording 7.887 g. (47.2%) of colorless prisms melting at 264 C. dec. (uncorr.). Concentration of the mother liquors yields a second crop of colorless prisms melting at 265 C. dec. (uncorr.) in a yield of 6.258 g. (37.4%) total yield is 14.145 g. (84.6%). Analysis for: C6 H9 N5 O; Calculated: C, 43.11; H, 5.42; N, 41.90; Found: C, 43.04; H, 5.35; N, 42.12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; acetic acid; In water; | EXAMPLE 7 1.36 g. of 4-amino-5-cyano-1,6-dihydro-2-methyl-pyrimidine are dissolved in 10 ml. of a 50% solution of acetic acid and treated with ca 10 mg. of iron (II) sulfate. To this mixture are added dropwise 1.5 ml. of 30% hydrogen peroxide in 4.5 ml. of water in such a manner that the reaction temperature does not exceed 30 C. The oxidation is completed when excess hydrogen peroxide is still detectable 10 minutes after the last addition. The excess hydrogen peroxide is decomposed with sodium bisulfate. The reaction mixture is subsequently adjusted to a pH of 6 by the addition of concentrated sodium hydroxide with cooling and stirring. The isolated 4-amino-5-cyano-2-methyl-pyrimidine, after washing with a small amount of ice-water and recrystallization from water with addition of decolorizing carbon, melts at 257-258 C. |
Tags: 698-29-3 synthesis path| 698-29-3 SDS| 698-29-3 COA| 698-29-3 purity| 698-29-3 application| 698-29-3 NMR| 698-29-3 COA| 698-29-3 structure
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