Dimethylformamide → 2-(Ethylthio)-9-(phenylmethyl)-9H-purin-6-amine

HRID 2269075Notes

Reaction equation

HRID 2269075 reaction equation
CN(C=O)C.[H-].[Na+].[CH2:8]([SH:10])[CH3:9].[NH2:11][C:12]1[N:20]=[C:19](Cl)[N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>[Cl-].[Na+].O>[NH2:11][C:12]1[N:20]=[C:19]([S:10][CH2:8][CH3:9])[N:18]=[C:17]2[C:13]=1[N:14]=[CH:15][N:16]2[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 183326882-(Ethylthio)-9-(phenylmethyl)-9H-purin-6-amineYield 82%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To DMF suspension (10 ml) containing sodium hydride (300 mg, 7.5 mmol, 60% in mineral oil) were added ethanethiol (2 ml, 27 mmol) and 6-amino-9-benzyl-2-chloropurine (100 mg, 0.39 mmol) in order. The mixture was stirred under heating at 110° C. for 3.5 hours. Brine was added thereto and the mixture was extracted with ethyl acetate. The organic layer was dried on magnesium sulfate, filtered and the solvent in the filtrate was evaporated. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (90 mg, yield 82%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent in the filtrate was evaporated
  5. customThe residue was purified with silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-000edacf744a4433b9f57bfb4ff79b2f
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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