Chlorosuccinimide → 3-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester

HRID 2172602ノート

反応式

HRID 2172602 の反応式
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=3)[N:13]=[C:12]2[CH3:27])[CH:5]=1.[Cl:29]N1C(=O)CCC1=O>C(O)(C)C.ClC(Cl)C(O)=O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[C:16](=[O:17])[C:15]([Cl:29])=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=3)[N:13]=[C:12]2[CH3:27])[CH:5]=1

参加物

5

反応物 2

HCID 31398ChlorosuccinimideHCID 866862884-methyl-3-[2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester

生成物 1

HCID 866862893-[5-chloro-2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-4-methyl-benzoic acid methyl ester収率 96%

試薬・触媒・溶媒 2

HCID 6597Dichloroacetic Acid触媒HCID 3776Isopropanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of 4-methyl-3-[2-methyl-4-(3-methyl-benzyloxy)-6-oxo-6H-pyrimidin-1-yl]-benzoic acid methyl ester from Step A (218 mg, 0.58 mmol) in isopropanol (2 mL) was added N-chlorosuccinimide (84 mg, 0.63 mmol) and 2 drops of dichloroacetic acid. The solution was heated at 60° C. for two hours. The solution was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated to provide the chlorinated product as a light yellow oil (230 mg, 78%). MS (M+H): 413

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe slurry was filtered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-fe035b0103084243a6c14f8ab6a9ce9b
出典データセット
uspto-grants-2015_06
特許番号
US09056110B2

反応ノート

読み込み中…