Sodium Methoxide → 6-(3-chloro-2-methoxypyridin-4-yl)-2-((2S)-2-(4-fluorophenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one

HRID 1091398ノート

反応式

HRID 1091398 の反応式
Cl[C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][C@@H:17]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[CH2:16]3)[N:12]([CH3:28])[C:11](=[O:29])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][O-:31].[Na+]>O1CCCC1>[Cl:8][C:7]1[C:2]([O:31][CH3:30])=[N:3][CH:4]=[CH:5][C:6]=1[C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][C@@H:17]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH2:16]2)[N:12]([CH3:28])[C:11](=[O:29])[CH:10]=1

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 57877719HCID 57877719、化合物

生成物 1

HCID 578776496-(3-chloro-2-methoxypyridin-4-yl)-2-((2S)-2-(4-fluorophenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one収率 50.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A suspension of 6-(2,3-dichloropyridin-4-yl)-2-((2S)-2-(4-fluorophenyl)morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.50 g, 1.15 mmol), and sodium methoxide (1.1 g, 20.4 mmol) in tetrahydrofuran (10 ml) was heated at 60° C. for 5 hours. The resulting suspension was partitioned between chloroform and brine and the aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish 6-(3-chloro-2-methoxypyridin-4-yl)-2-((2S)-2-(4-fluorophenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.27 g, 0.58 mmol, 50%) as white crystals.

後処理

  1. customThe resulting suspension was partitioned between chloroform and brine
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting 5-10% methanol in chloroform

出典と根拠

ORDレコード
ord-42f526c4d7b448fa99ee16304e3c9fc9
出典データセット
uspto-grants-2012_03
特許番号
US08129377B2

反応ノート

読み込み中…