Phosphorus oxychloride → N-(4-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-yl)acetamide

HRID 1517461ノート

反応式

HRID 1517461 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]=[C:13]([NH:19][C:20](=[O:22])[CH3:21])[NH:14][C:15](=O)[C:16]=3[N:17]=2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:34]>O1CCOCC1>[Cl:34][C:15]1[C:16]2[N:17]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]=[CH:10][C:11]=2[N:12]=[C:13]([NH:19][C:20](=[O:22])[CH3:21])[N:14]=1

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 1360008912-acetamido-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one

生成物 1

HCID 57698346N-(4-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidin-2-yl)acetamide収率 52.6%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a suspension of N-[6-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-pyrido[3,2-d]pyrimidin-2-yl]-acetamide (0.77 g, 2.58 mmol) and DIEA (1.34 mL, 7.74 mmol) in dioxane (25 mL) was added POCl3 (0.73 mL, 7.74 mmol). The mixture was heated to 80° C. for 30 minutes. After the removal of solvent, the residue was dissolved in ethyl acetate (200 mL) and the solution was filtered through a short column with silica gel. The column was additionally washed with ethyl acetate. The filtrate and washings were combined and concentrated. The precipitate formed was isolated by filtration to give the pure title compound as a brown solid (0.43 g, yield 43%) which was characterised as follows: MS (m/z) 317.0 [M+H]+.

後処理

  1. customAfter the removal of solvent
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. filtrationthe solution was filtered through a short column with silica gel
  4. washThe column was additionally washed with ethyl acetate
  5. concentrationconcentrated
  6. customThe precipitate formed
  7. customwas isolated by filtration

出典と根拠

ORDレコード
ord-06f7b2309fec4d1487012e95de5d0852
出典データセット
uspto-grants-2012_07
特許番号
US08232278B2

反応ノート

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