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CAS No. : | 156-83-2 | MDL No. : | MFCD00006097 |
Formula : | C4H5ClN4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QJIUMVUZDYPQRT-UHFFFAOYSA-N |
M.W : | 144.56 | Pubchem ID : | 67432 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 35.85 |
TPSA : | 77.82 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) : | -6.85 cm/s |
Log Po/w (iLOGP) : | 0.93 |
Log Po/w (XLOGP3) : | 0.47 |
Log Po/w (WLOGP) : | 0.31 |
Log Po/w (MLOGP) : | -0.22 |
Log Po/w (SILICOS-IT) : | 0.28 |
Consensus Log Po/w : | 0.35 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.53 |
Solubility : | 4.31 mg/ml ; 0.0298 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.67 |
Solubility : | 3.07 mg/ml ; 0.0212 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.53 |
Solubility : | 4.3 mg/ml ; 0.0297 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.92 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
85% | at 97℃; for 17 h; | 2,4-Diamino-6-hydroxypyrimidine (1) (1.00 g, 7.93 mmol) wasadded to POCl3 (9 mL), and stirred at 97 C for 17 h. The reaction solution was added to ice waterslowly, and then stirred at 90 C for 1 h. The pH of this solution was adjusted to 8 with NaOH,and then it was extracted with EtOAC (150 mL 3). The combined organic layers were dried withNa2SO4, filtered and concentrated to give white solid 0.97 g, yield 85percent. m.p. 200.2–200.4 C; IR(KBr): max/cm-1 3449 (NH), 3327 (NH), 1642 (C=N), 1581 (C=C), 1551 (C=C), 795 (C-Cl); 1H-NMR(DMSO-d6) δ6.57 (s, 2H, NH2), 6.31 (s, 2H, NH2), 5.69 (s, 1H, Ar-H); ES-MS 145.0 (M + H)+; HRMSCalcd. for C16H20ClN4O3+ 145.0281, found 145.0276. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47.3% | With sodium hydroxide; potassium carbonate; trichlorophosphate In tetrahydrofuran; water; acetone | b) Preparation of 6-chloro-2,4-diaminopyrimidine In a 200 l multi-purpose glass lined reactor, connected to a sodium hydroxide trap, phosphorous oxychloride (88 l = 147 kg) and 2,6-diamino-4-hydroxypyrimidine (22.2 kg) were charged. The suspension was heated to reflux under stirring for 5 hours, then part of the oxychloride (22 l) was distilled at room pressure. The residue was cooled and left to stand overnight, then heated to pre-fluidize the viscous oil, which was charged into a flask provided with a blowdown valve on the bottom. The flask was transferred over a 1000 l glass lined reactor containg 290 l of water. The heated oil was added under stirring, adjusting cooling so that temperature approached as much as possible to 100°C around the end of the addition. At the end of the addition, the solution was refluxed for 10 min., cooled and added with 230 kg of potassium carbonate to a pH from 8.5 to 9.0, under suction. The solid was centrifuged without washing the cake, granulated and dried in oven at 70°C. The dried solid was kneaded at ebollition for 2 hours in 100 l of tetrahydrofuran, the suspension was cooled to room temperature and filtered on a filter press, on which a celite or charcoal layer had been previously placed. The pressed solid was then discharged into the reactor and subjected to the same treatment. The collected filtrates were concentrated to dryness at room pressure and the residual solid was kneaded at ebollition for 30 min. in 25 l of acetone, the suspension was cooled and pump-filtered, and dried first in the air, then in oven at 70°C. 11.9 kg (yield 47.3percent) of a light cream solid was obtained, unitary in T.L.C. (CHCl35/MeOH 4/AcOEt 1): Rf 0.6; melting at 197-199°C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | for 44 h; Reflux | To a solution of 9.2 g (0.40 mol) sodium in 320 ml methanol were added 28.9 g (0.20 mol) 2,4-diamino-6-chloropyrimidine. The mixture was heated under reflux with stirring for 44 h. After the reaction was ended the precipitated NaCl was separated off and the solution was concentrated to dryness. The residue in 300 ml ethanol was heated to boiling and filtered hot. The product precipitated out of the filtrate on standing overnight. Recrystallization of the mother liquor likewise afforded product. After drying, 6-methoxy-2,4-diaminopyrimidine was obtained as a white solid (58.8 g, 84percent). m.pt.: 166-169° C. 1H-NMR (300 MHz, d6-DMSO): δ=3.18 (s, 3 H, 6-OMe), 5.06 (s, 1H, 5-H), 5.94 (s, 2 H, NH2), 6.05 (s, 2 H, NH2). 13C-NMR (125 MHz, d6-DMSO): δ=52.8 (6-OMe), 76.1 (5-C), 163.3 (2-C), 166.3 (4-C), 170.8 (6-C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | for 6 h; Reflux | To a solution of NaH (2.77 g, 69.2 mmol) in ethanol (150 ml) was added 2,6-diamino-4-chloropyrimidine (5.0 g, 34.6 mmol). The mixture was refluxed for 6 h. After cooling, the solution was neutralized with a 5-6 N HCl solution in isopropyl alcohol. After removing the solvents in vacuo, the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 40:1), yielding the title compound as a white solid (4.0 g, 75percent). Mp 164-165 °C. 1H NMR (300 MHz, DMSO, 25 °C): δ = 6.00 (s, 2H, NH2), 5.88 (s, 2H, NH2), 5.03 (s, 1H, CH), 4.13 (q, J = 7.1 Hz, 2H, CH2), 1.22 (t, J = 7.1 Hz, 3H, CH3) ppm. 13C NMR (75 MHz, DMSO, 25 °C): δ = 170.0, 165.9, 162.9, 76.1, 60.2, 14.7 ppm. HRMS: calcd for C6H11N4O [M+H]+ 155.09329, found 155.09260. |
72% | at 160℃; for 6 h; | EXAMPLE 54 Synthesis of 2,6-diamino-4-ethoxy-pyrimidine To a solution of sodium (1.05 g) in ethanol (50 ml) was added 4-chloro-2,6-diaminopyrimidine (6 g, 41.4 mmoles).The resulting solution was heated in a reactor for 6 hours at 160° C. The reaction mixture was cooled down and the precipitated sodium chloride was filtered off.The filtrate was concentrated and precipitated from ethanol (two times), affording the pure title compound as a white solid (4.53 g, 72percent yield).The spectral data are identical to those described e.g. by W. Pfleiderer et al. in Chem. Ber. (1961) 94, 12. |
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