Sodium borohydride → 2-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methyl-5-phenyl thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1091694노트

반응식

HRID 1091694 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[C:3]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+]>C(Cl)Cl.CO>[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[C:3]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:2]([CH3:1])[S:23][C:5]=3[N:6]=2)[CH:16]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydride2회HCID 866303981-((6-Methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 665916232-((4-(Hydroxymethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methyl-5-phenyl thieno[2,3-d]pyrimidin-4(3H)-one수율 10.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 1-((6-methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde (97 mg, 0.232 mmol) in DCM (2 mL) and MeOH (2 mL) was added sodium borohydride (26 mg, 0.696 mmol) and the mixture was stirred overnight. Sodium borohydride (53 mg, 1.39 mmol) was added and the mixture was stirred for a further 20 h. The reaction mixture was quenched with water and concentrated in vacuo. The residue was taken up in 1:1 DMSO:MeCN, filtered and purified by preparative LCMS to give the title product as a white solid (10 mg, 0.024 mmol, 10%).

후처리

  1. stirringthe mixture was stirred for a further 20 h
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated in vacuo
  4. filtrationMeCN, filtered
  5. custompurified by preparative LCMS

출처 및 근거

ORD 기록
ord-ab603b70f8094f3980c67aef3faf229f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129397B2

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