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 1091694ノート

反応式

HRID 1091694 の反応式
[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

参加物

5

反応物 2

HCID 4311764Sodium borohydride2 回HCID 866303981-((6-Methyl-4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ab603b70f8094f3980c67aef3faf229f
出典データセット
uspto-grants-2012_03
特許番号
US08129397B2

反応ノート

読み込み中…