Ethanol → 6-[cyclohexyl(cyclopropylmethyl)amino]-N-(2-methylphenyl)pyrimidine-4-carboxamide

HRID 1746657

반응식

HRID 1746657 반응식
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]1

참가 물질

5

반응물 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 573244341-(1-Cyclohexylcyclopropyl)methanamineHCID 594470936-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide2회

생성물 1

HCID 594470896-[cyclohexyl(cyclopropylmethyl)amino]-N-(2-methylphenyl)pyrimidine-4-carboxamide

반응 조건

온도
160 °C

실험 절차

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 compound as a beige solid.

후처리

  1. additionAt the end of addition the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with NH4Cl, NaHCO3 and brine
  6. customdried on magnesium sulfate
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-86e7fc18656e40bdb59da635b15c5d4a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150519B2

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