Dicyclohexylcarbodiimide → 3-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione

HRID 1380415ノート

反応式

HRID 1380415 の反応式
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4](O)=[O:5].[CH3:10][NH:11][C:12]([NH2:14])=[O:13].C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH3:10][N:11]1[C:4](=[O:5])[CH:3]([C:2]([F:9])([F:8])[F:1])[CH2:7][NH:14][C:12]1=[O:13].[CH3:10][N:11]1[CH2:7][CH:3]([C:2]([F:9])([F:8])[F:1])[C:4](=[O:5])[NH:14][C:12]1=[O:13]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 11719MethylureaHCID 5876942-(Trifluoromethyl)acrylic acid

生成物 2

HCID 130049793-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione収率 43%HCID 130049801-Methyl-5-(trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione収率 18%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

A mixture of α-trifluoromethylacrylic acid (700 mg; 5.0 mmoles) and methylurea (370 mg; 5.0 mmoles) in DMF (5 ml) was heated at 80° C. with stirring for 3 hours. After cooling to 0° C., a solution of dicyclohexylcarbodiimide (DCC) (1.05 g; 5.1 mmoles) in 3 ml of DMF was added dropwise. The mixture was stirred for 1 hour, and the precipitated solid was filtered off and washed with ethyl acetate. The solvent was evaporated under reduced pressure from the combined filtrates. The residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:3) to give 424 mg (yield: 43%) of 3-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-2) and 174 mg (yield: 18%) of 1-methyl-5-trifluoromethyl-5,6-dihydrouracil (OF-3).

後処理

  1. temperatureAfter cooling to 0° C.
  2. stirringThe mixture was stirred for 1 hour
  3. filtrationthe precipitated solid was filtered off
  4. washwashed with ethyl acetate
  5. customThe solvent was evaporated under reduced pressure from the combined filtrates
  6. customThe residue was purified by a column chromatography on silica gel (ethyl acetate:chloroform=1:3)

出典と根拠

ORDレコード
ord-1603c044245149dd8d72c576887484f6
出典データセット
uspto-grants-1986_04
特許番号
US04581452

反応ノート

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