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

HRID 1091688ノート

反応式

HRID 1091688 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:6][NH:5][N:4]=1.CC(C)([O-])C.[K+].Cl[CH2:21][C:22]1[NH:23][C:24](=[O:32])[C:25]2[CH:30]=[C:29]([CH3:31])[S:28][C:26]=2[N:27]=1>C1COCC1>[OH:11][C:8]([C:7]1[C:3]([C:2]([F:1])([F:12])[F:13])=[N:4][N:5]([CH2:21][C:22]2[NH:23][C:24](=[O:32])[C:25]3[CH:30]=[C:29]([CH3:31])[S:28][C:26]=3[N:27]=2)[CH:6]=1)([CH3:9])[CH3:10]

参加物

5

反応物 3

HCID 64916832-(Chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-oneHCID 23665647Potassium tert-butoxideHCID 178458810HCID 178458810、化合物

生成物 1

HCID 665916902-((4-(2-Hydroxypropan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)methyl)-6-methyl thieno[2,3-d]pyrimidin-4(3H)-one収率 4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-(3-(trifluoromethyl)-1H-pyrazol-4-yl)propan-2-ol (73 mg, 0.376 mmol) and potassium tert-butoxide (127 mg, 1.13 mmol) in THF (2 mL) was stirred for ˜2 min. To this was added 2-(chloromethyl)-6-methylthieno[2,3-d]pyrimidin-4(3H)-one (81 mg, 0.376 mmol) and the resultant mixture was stirred for 18 h. The reaction mixture was quenched with saturated NH4Cl solution and concentrated in vacuo. The residue was partitioned between DCM and water and the organic layer was separated. The aqueous layer was extracted with further DCM and the combined organics were washed with saturated brine, dried over MgSO4, filtered and concentrated in vacuo to give a light yellow gum. The gum was purified by preparative LCMS to give the product as a white solid (5 mg, 0.014 mmol, 4%).

後処理

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between DCM and water
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with further DCM
  6. washthe combined organics were washed with saturated brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a light yellow gum
  11. customThe gum was purified by preparative LCMS

出典と根拠

ORDレコード
ord-9b52bf88e9314f129e87b4f8ace20b5f
出典データセット
uspto-grants-2012_03
特許番号
US08129397B2

反応ノート

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