Potassium Carbonate → N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide

HRID 1094719ノート

反応式

HRID 1094719 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[S:25][C:19]3[N:20]=[CH:21][NH:22][C:23](=[O:24])[C:18]=3[C:17]=2[CH3:26])=[O:15])[CH2:10][CH2:9]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:34][C:35]([NH:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:39]=1[F:45])=[O:36]>CC#N>[F:45][C:39]1[CH:40]=[C:41]([F:44])[CH:42]=[CH:43][C:38]=1[NH:37][C:35](=[O:36])[CH2:34][N:22]1[C:23](=[O:24])[C:18]2[C:17]([CH3:26])=[C:16]([C:14]([N:11]3[CH2:10][CH2:9][N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])[CH2:13][CH2:12]3)=[O:15])[S:25][C:19]=2[N:20]=[CH:21]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 7358542-chloro-N-(2,4-difluorophenyl)acetamideHCID 160032576-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one

生成物 1

HCID 59842858N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
130 °C

実験手順

To a suspension of 6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methylthieno[2,3-d]pyrimidin-4(3H)-one, (0.06 g, 0.16 mmol) in CH3CN (0.5 mL) was added K2CO3 (22 mg, 0.16 mmol), KI (29 mg, 0.17 mmol), and 2-chloro-N-(2,4-difluorophenyl)acetamide, (36 mg, 0.16 mmol). The reaction mixture was heated at 130° C. for 25 min in a microwave reactor. The reaction was quenched with H2O (25 mL) and the aqueous layer was extracted with EtOAc (25 mL). The organic layer was washed with brine (25 mL), dried over Na2SO4 and concentrated. The crude material was purified by flash chromatography (Et2O:DCM, 1:1) providing 30 mg of pure N-(2,4-difluorophenyl)-2-(6-(4-(2-fluorophenyl)piperazine-1-carbonyl)-5-methyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)acetamide, (yield: 35%).

後処理

  1. customThe reaction was quenched with H2O (25 mL)
  2. extractionthe aqueous layer was extracted with EtOAc (25 mL)
  3. washThe organic layer was washed with brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (Et2O:DCM, 1:1)

出典と根拠

ORDレコード
ord-f2bb043b49d941cb8cb86831a0ad4fec
出典データセット
uspto-grants-2012_03
特許番号
US08133998B2

反応ノート

読み込み中…