Water → 3-iodo-1-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 243315ノート

反応式

HRID 243315 の反応式
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.Cl[CH2:13][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[N:15]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH2:13][C:14]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:17]3[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=3[N:15]=2)[N:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazoleHCID 178508725HCID 178508725、化合物

生成物 1

HCID 681579743-iodo-1-((1-phenyl-1H-benzo[d]imidazol-2-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine収率 52.1%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamine (11.0 g, 41.1 mmol), 2-(chloromethyl)-1-phenyl-1H-benzo[d]imidazole (10.0 g, 41.4 mmol) and K2CO3 (6.0 g, 43.4 mmol) in DMSO (60 mL) was stirred at room temperature overnight. Then the mixture was added H2O (100 mL) and extracted with EtOAc (100 mL×3). The combined organic layers were concentrated in vacuo, and the residue was purified by column chromatography on silica gel (PE:EtOAc=2:1) to give 141 (10.0 g, yield 52%) as a yellow solid. LCMS (ESI), M+H+=466.04. 1HNMR (400 MHz, CDCl3) δ 5.783 (s, 2H), 5.785 (s, 2H), 7.068-7.090 (q, J=0.8 Hz, 1H), 7.088-7.307 (m, 3H), 7.362-7.422 (m, 4H), 7.800-7.822 (d, J=0.8 Hz, 1H), 8.219-8.221 (d, J=1.2 Hz, 2H)

後処理

  1. extractionextracted with EtOAc (100 mL×3)
  2. concentrationThe combined organic layers were concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (PE:EtOAc=2:1)

出典と根拠

ORDレコード
ord-bc8d909801174b83b236d0a444d98f5f
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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