Dichloromethane → 5-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 2181347

반응식

HRID 2181347 반응식
[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]=2[S:4][C:3]=1[CH:18](O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26].FC(F)(F)C(O)=O.C(Cl)Cl>C([SiH](CC)CC)C>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]=2[S:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:26])([F:27])[F:28]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 52825285-Bromo-6-[hydroxy[2-(trifluoromethyl)phenyl]methyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 114429025-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione수율 84.5%

시약·촉매·용매 1

HCID 12052Triethylsilane용매

실험 절차

5-Bromo-6-{hydroxy[2-(trifluoromethyl)phenyl]methyl}-1-isobutyl-3-methyl-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (33.47 g) was dissolved in triethyl silane (100 mls) and cooled to 0° C. before trifluoroacetic acid (100 mls) was added dropwise. After complete addition the resultant thick suspension was diluted by the addition of DCM (100 mls) and the reaction was stirred at room temperature for 18 hours. The reaction mixture was then concentrated in vacuo and partitioned between DCM and 50% aqueous sodium hydrogen carbonate. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated in vacuo. The resultant off white solid was stirred vigorously with isohexane for 1 hour before being collected by filtration to yield 27.286 g (84.5%) of the subtitle compound.

후처리

  1. additionwas added dropwise
  2. additionAfter complete addition the resultant thick suspension
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. custompartitioned between DCM and 50% aqueous sodium hydrogen carbonate
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. stirringThe resultant off white solid was stirred vigorously with isohexane for 1 hour
  10. filtrationbefore being collected by filtration

출처 및 근거

ORD 기록
ord-0ab8523d44fa4123b1094f5e6afdf4e9
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890923B2

연결된 노트

불러오는 중…