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

HRID 243346노트

반응식

HRID 243346 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-c6d474812cd145e0807bac9f0f7204a6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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