Sodium hydride → 9-((3-o-tolylbenzo[b]thiophen-2-yl)methyl)-9H-purin-6-amine

HRID 243346ノート

反応式

HRID 243346 の反応式
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([NH:7][CH:8]=[N:9]2)=[N:5][CH:4]=1.CS(O[CH2:18][C:19]1[S:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[C:20]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34])(=O)=O>CN(C=O)C>[C:29]1([CH3:34])[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[S:23][C:19]=1[CH2:18][N:7]1[CH:8]=[N:9][C:10]2[C:6]1=[N:5][CH:4]=[N:3][C:11]=2[NH2:12]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 86668875(3-o-Tolylbenzo[b]thiophen-2-yl)methyl methanesulfonateHCID 178508693HCID 178508693、化合物

生成物 1

HCID 601620369-((3-o-tolylbenzo[b]thiophen-2-yl)methyl)-9H-purin-6-amine収率 67.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

NaH (60% in mineral oil, 16 mg, 0.39 mmol) was added in one portion to a mixture of 9H-purin-6-ylamine (49 mg, 0.36 mmol) in DMF (5 mL) at RT. After 5 min stirring, a solution of methanesulfonic acid 3-o-tolylbenzo[b]thiophen-2-ylmethyl ester from Example 27 (100 mg, 0.30 mmol) in DMF (1 mL) was added dropwise and stirring at RT was continued for 19 h. The reaction mixture was then quenched by addition of water and a solid formed. The precipitated was collected by filtration and was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) affording 167 as a white solid (75 mg, 67%). LCMS: RT 4.13 min [M+H]+ 372.1. 1H NMR (DMSO, 400 MHz): δ 8.11 (1H, s), 7.96-7.88 (2H, m), 7.45-7.30 (6H, m), 7.23 (2H, s), 7.12-7.07 (1H, m), 5.46 (1H, d, J=16.2 Hz), 5.38 (1H, d, J=16.2 Hz), 1.99 (3H, s)

後処理

  1. stirringstirring at RT
  2. waitwas continued for 19 h
  3. customThe reaction mixture was then quenched by addition of water
  4. customa solid formed
  5. filtrationThe precipitated was collected by filtration
  6. customwas purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc)

出典と根拠

ORDレコード
ord-c6d474812cd145e0807bac9f0f7204a6
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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