Methanol → 2-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1091691노트

반응식

HRID 1091691 반응식
[CH3:1][C:2]1[S:23][C:5]2[N:6]=[C:7]([CH2:11][N:12]3[CH:16]=[C:15]([CH:17]=[O:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]3)[NH:8][C:9](=[O:10])[C:4]=2[CH:3]=1.CO.[BH4-].[Na+]>C(Cl)Cl>[OH:18][CH2:17][C:15]1[C:14]([C:19]([F:20])([F:22])[F:21])=[N:13][N:12]([CH2:11][C:7]2[NH:8][C:9](=[O:10])[C:4]3[CH:3]=[C:2]([CH3:1])[S:23][C:5]=3[N:6]=2)[CH:16]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866303971-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 665915302-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one수율 28%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1-((6-Methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (100 mg, 0.292 mmol) was dissolved in a 1:1 DCM:MeOH solution (2 mL) and sodium borohydride (33 mg, 0.876 mmol) added. After 30 min the mixture was quenched by addition of water (1 mL) then concentrated in vacuo. Purification by flash column chromatography-silica gel and elution with 3% MeOH:DCM resulted in a white solid which was recrystallised from isopropanol and freeze dried to give the title compound as a white solid (28 mg, 0.081 mmol, 28%).

후처리

  1. customAfter 30 min the mixture was quenched by addition of water (1 mL)
  2. concentrationthen concentrated in vacuo
  3. customPurification
  4. washby flash column chromatography-silica gel and elution with 3% MeOH
  5. customDCM resulted in a white solid which
  6. customwas recrystallised from isopropanol and freeze
  7. customdried

출처 및 근거

ORD 기록
ord-2358a72046234964bdf484dffe235f22
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129397B2

반응 노트

불러오는 중…