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

HRID 1946675노트

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HRID 1946675 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 compounds 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-4750883bf5cf45919692937d605ab8c2
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399448B2

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