Ethanol → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(2-methylphenyl)pyrimidine-4-carboxamide
Reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[O:9])[CH:3]=1.CC[N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])C.[CH:27]1(C2(CN)CC2)[CH2:32]CCC[CH2:28]1.[CH3:38][CH2:39]O>>[CH:24]1([N:20]([CH2:21][CH:23]2[CH2:39][CH2:38]2)[C:2]2[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])=[O:9])[CH:3]=2)[CH2:25][CH2:32][CH2:27][CH2:28][CH2:26]1Participants
5
Conditions
- Temperature
- 160 °C
Procedure
A solution of 6-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide (Intermediate 18; 3.00 g; 12.11 mmol) in EtOH (30 ml) was treated with DIEA (4.17 ml; 24.2 mmol) and cyclohexyl-cyclopropanemethyl-amine (Chembridge; 3.71 g; 24.2 mmol) and heated at 160° C. for 1 h. At the end of addition the reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. The combined organic layers were washed with NH4Cl, NaHCO3 and brine, dried on magnesium sulfate and evaporated in vacuo to afford the title compound as a brown solid, which was purified by precipitation from cyclohexane to afford the title compounds as a beige solid.
Workup
- additionAt the end of addition the reaction mixture
- concentrationwas concentrated in vacuo
- additiondiluted with water
- extractionextracted with EtOAc
- washThe combined organic layers were washed with NH4Cl, NaHCO3 and brine
- customdried on magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-4750883bf5cf45919692937d605ab8c2
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399448B2
Reaction notes
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