Sodium hydride → 9-((3-phenyl-1-tosyl-1H-indol-2-yl)methyl)-9H-purin-6-amine

HRID 242879Notes

Reaction equation

HRID 242879 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([NH:5][CH:6]=[N:7]2)=[N:3][CH:2]=1.[H-].[Na+].Br[CH2:14][C:15]1[N:16]([S:30]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)(=[O:32])=[O:31])[C:17]2[C:22]([C:23]=1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2>CN(C=O)C>[C:24]1([C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([S:30]([C:33]3[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=3)(=[O:32])=[O:31])[C:15]=2[CH2:14][N:5]2[CH:6]=[N:7][C:8]3[C:4]2=[N:3][CH:2]=[N:1][C:9]=3[NH2:10])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 681573292-Bromomethyl-3-phenyl-1-(toluene-4-sulfonyl)-1H-indoleHCID 178508693HCID 178508693, compound

Product 1

HCID 681569779-((3-phenyl-1-tosyl-1H-indol-2-yl)methyl)-9H-purin-6-amineYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred mixture of 9H-purin-6-ylamine (130 mg, 0.98 mmol) in DMF (5 mL) under an argon atmosphere was added NaH (60% in mineral oil, 40 mg, 0.98 mmol). After stirring for 10 min at RT, 2-bromomethyl-3-phenyl-1-(toluene-4-sulfonyl)-1H-indole (430 mg, 0.98 mmol) in DMF (10 mL) was added and stirring continued for 15 min. The crude reaction mixture was loaded onto an Isolute® SCX-2 cartridge then washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) affording the title compound as a white solid (370 mg, 77%). LCMS (Method C): RT 3.16 min [M+H]+ 495.1.

Workup

  1. stirringstirring
  2. waitcontinued for 15 min
  3. customThe crude reaction mixture
  4. washthen washed with MeOH
  5. washthe product eluted with 2M NH3/MeOH
  6. additionThe product containing fractions
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-74ac40b9f41b4594bf422074b6205ac4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…