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

HRID 1380415노트

반응식

HRID 1380415 반응식
[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]

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1603c044245149dd8d72c576887484f6
출처 데이터셋
uspto-grants-1986_04
특허 번호
US04581452

반응 노트

불러오는 중…