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

HRID 243345Notes

Reaction equation

HRID 243345 reaction equation
[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.[C:13]1([C:19]2[C:20]3[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=3[S:22][C:23]=2[CH2:24]OS(C)(=O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[C:13]1([C:19]2[C:20]3[CH:33]=[CH:32][CH:31]=[CH:30][C:21]=3[S:22][C:23]=2[CH2:24][N:7]2[CH:8]=[N:9][C:10]3[C:6]2=[N:5][CH:4]=[N:3][C:11]=3[NH2:12])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86668872(3-Phenylbenzo[b]thiophen-2-yl)methyl methanesulfonateHCID 178508693HCID 178508693, compound

Product 1

HCID 601620359-((3-phenylbenzo[b]thiophen-2-yl)methyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60% in mineral oil, 15 mg, 0.377 mmol) was added in one portion to a mixture of 9H-purin-6-ylamine (47 mg, 0.345 mmol) in DMF (3 mL) at RT. After 5 min stirring, a solution of methanesulfonic acid 3-phenylbenzo[b]thiophen-2-ylmethyl ester from Example 26 (100 mg, 0.314 mmol) in DMF (2 mL) was added dropwise and stirring at RT was continued for 30 min. 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) and triturated from diethyl ether affording 166 as a white solid (52 mg, 46%). LCMS: RT 3.99 min [M+H]+ 358.1. 1H NMR (DMSO, 400 MHz): δ 8.15 (1H, s), 8.06 (1H, s), 7.98-7.92 (1H, m), 7.64-7.59 (4H, m), 7.57-7.46 (2H, m), 7.42-7.37 (2H, m), 7.27 (2H, s), 5.63 (2H, s)

Workup

  1. stirringstirring at RT
  2. waitwas continued for 30 min
  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)
  7. customtriturated from diethyl ether affording 166 as a white solid (52 mg, 46%)

Sources & evidence

ORD record
ord-77307e9f938b43afa7fc5ca54a7d004c
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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