Methyl iodide → 4-(5-amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-methyl-N-p-tolylpiperazine-1-carboxamide

HRID 1507887ノート

反応式

HRID 1507887 の反応式
[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)=[O:24])[CH2:19][CH2:18]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=1.[H-].[Na+].[CH3:35]I>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([N:25]([CH3:35])[C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)=[O:24])[CH2:19][CH2:18]2)[C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[S:8][C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 469163824-(5-Amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-(p-tolyl)piperazine-1-carboxamide

生成物 1

HCID 569408814-(5-amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-methyl-N-p-tolylpiperazine-1-carboxamide収率 43.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 4-(5-amino-2-(pyridin-3-yl)thiazolo[5,4-d]pyrimidin-7-yl)-N-p-tolylpiperazine-1-carboxamide (90 mg, 0.2 mmol) in DMF (5 ml) was added NaH (60%, 12 mg, 0.31 mmol). The resulting mixture was stirred at room temperature for 10 minutes. Then, methyl iodide (0.3 mmol) was added to the mixture. After stirring at room temperature for 30 minutes, the solvents were evaporated in vacuo and the crude residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio of 1/30), yielding the pure title compound as yellowish solid (40 mg, 43%).

後処理

  1. stirringAfter stirring at room temperature for 30 minutes
  2. customthe solvents were evaporated in vacuo
  3. customthe crude residue was purified by flash chromatography on silica
  4. additiona mixture of methanol and dichloromethane (in a ratio of 1/30),

出典と根拠

ORDレコード
ord-08ee4ce1044446b1a52ec59582d5c56e
出典データセット
uspto-grants-2015_12
特許番号
US09221822B2

反応ノート

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