Pyridine → [2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl acetate

HRID 1508715ノート

反応式

HRID 1508715 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([CH2:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:10]=2)=[CH:4][C:3]=1[CH2:24][OH:25].[C:26](Cl)(=[O:28])[CH3:27].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[C:26]([O:25][CH2:24][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[C:14]([CH2:15][CH3:16])=[C:13]([CH3:17])[N:12]=[C:11]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[N:10]=2)[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:28])[CH3:27]

参加物

6

反応物 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 90112603[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol

生成物 1

HCID 90113035[2-Bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methyl acetate収率 72.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒

実験手順

A 18-mL vial was charged with [2-bromo-5-[[2-(5-chloro-2-thienyl)-5-ethyl-6-methyl-pyrimidin-4-yl]amino]phenyl]methanol (93 mg, 0.21 mmol), acetyl chloride (100 mg, 1.27 mmol, 6 eq.). Pyridine (1 ml) was added followed by 4-(dimethylamino)pyridine (5 mg, 0.2 eq.). The resulting mixture was stirred at rt for 2 hr. Then water was (5 ml) added. The precipitate was collected and washed with water. The crude product was purified by chromatography on silica gel using dichloromethane as eluent to give the tile compound (73 mg, 72% yield).

後処理

  1. additionadded
  2. customThe precipitate was collected
  3. washwashed with water
  4. customThe crude product was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-4ef87933092a457e89f43f5a0fb30ce4
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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