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

HRID 1946675

反応式

HRID 1946675 の反応式
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

参加物

5

反応物 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 573244341-(1-Cyclohexylcyclopropyl)methanamineHCID 594470936-chloro-N-(2-methylphenyl)pyrimidine-4-carboxamide2 回

生成物 1

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

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4750883bf5cf45919692937d605ab8c2
出典データセット
uspto-grants-2013_03
特許番号
US08399448B2

関連ノート

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