Triethylamine → 6-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

HRID 1946664

反応式

HRID 1946664 の反応式
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl:17][C:18]1[N:23]=[CH:22][N:21]=[C:20]([C:24](Cl)=[O:25])[CH:19]=1.ClC1N=CN=C(C(NC2C=CC(O)=CC=2)=O)C=1>ClCCl>[Cl:17][C:18]1[N:23]=[CH:22][N:21]=[C:20]([C:24]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[O:25])[CH:19]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 178194-Amino-m-cresolHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

生成物 1

HCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A cooled (0° C.) solution of 4-amino-m-cresol (Fluka, 4.17 g, 33.9 mmol) and triethylamine (23.6 mL, 0.170 mol) in dry dichloromethane (100 mL) was treated with 6-chloropyrimidine-4-carbonyl chloride, obtained as described above for Intermediate 7, step 1 (6.0 g, 34 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. The combined organic layers were dried on magnesium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (silica) using as eluent petroleum ether/EtOAc to afford the title compound as yellow solid.

後処理

  1. customobtained
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. customThe combined organic layers were dried on magnesium sulfate
  6. customevaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica)

出典と根拠

ORDレコード
ord-293e601e98894baca4aea202277ee4ff
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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