Dimethylformamide dimethyl acetal → (E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate

HRID 41479

反応式

HRID 41479 の反応式
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH3:15][N:16]([CH:18](OC)OC)[CH3:17]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](/[CH:14]=[CH:15]/[N:16]([CH3:18])[CH3:17])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 78373Dimethylformamide dimethyl acetalHCID 188208Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylate

生成物 1

HCID 86657908(E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate収率 62%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Methyl-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 3 (18.0 g, 84.8 mmol) was dissolved in DMF (50 mL), N,N-Dimethylformamidedimethylacetal (22.5 mL, 170 mmol) and stirred at reflux for 3 hours. Then mixture was concentrated, the residue was dissolved in TCM, washed with water, dried, filtered, and concentrated. The product was purified by crystallization from ether to yield in a colorless solid (14.0 g, 52.5 mmol, 62%).

後処理

  1. temperatureat reflux for 3 hours
  2. concentrationThen mixture was concentrated
  3. dissolutionthe residue was dissolved in TCM
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by crystallization from ether

出典と根拠

ORDレコード
ord-dc974b9b448b4f40ae01977f5f513159
出典データセット
uspto-grants-2013_09
特許番号
US08530650B2

関連ノート

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