Water → 3-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

HRID 1749095ノート

反応式

HRID 1749095 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:7](=[O:12])[NH:8][CH2:9][C:10]=2[N:11]=1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C=O)C>[CH2:21]([N:8]1[CH2:9][C:10]2[N:11]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]1=[O:12])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 709815066-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one

生成物 1

HCID 709805483-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one収率 67.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (120 mg, 0.5 mmol, 1.0 equiv) in DMF (3 mL) was added sodium hydride (60% in mineral oil, 24 mg, 0.6 mmol, 1.2 equiv) and the reaction mixture was stirred for 1 h. Benzyl bromide (70 μL, 0.6 mmol, 1.2 equiv) was added and the mixture was stirred for 16 h. H2O was added and the product was extracted with EtOAc. The organic phase was washed with, brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-40%) to afford 3-benzyl-6-fluoro-1-phenyl-3,4-dihydro-1H-pyrido[3,2-d]pyrimidin-2-one (112 mg). MS: [M+H]+=334.

後処理

  1. stirringthe mixture was stirred for 16 h
  2. extractionthe product was extracted with EtOAc
  3. washThe organic phase was washed with, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-40%)

出典と根拠

ORDレコード
ord-5e48c906bbbc48ba990ebca7674799b7
出典データセット
uspto-grants-2015_10
特許番号
US09155743B2

反応ノート

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