Dimethylformamide → HCID 18332709, compound

HRID 2269078Notes

Reaction equation

HRID 2269078 reaction equation
CN(C=O)C.[H-].[Na+].[CH3:8][CH:9]([CH3:12])[CH2:10][SH:11].[NH2:13][C:14]1[N:22]=[C:21](Cl)[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cl-].[Na+].O>[NH2:13][C:14]1[N:22]=[C:21]([S:11][CH2:10][CH:9]([CH3:12])[CH3:8])[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10558Isobutyl mercaptanHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332709HCID 18332709, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To DMF suspension (10 ml) containing sodium hydride (300 mg, 7.5 mmol, 60% in mineral oil) were added 2-methylpropane-1-thiol (1 ml, 11 mmol) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred under heating at 100° C. for 5 hours. Brine was added thereto and the mixture was extracted with chloroform. The organic layer was dried on magnesium sulfate, filtered and the solvent in the filtrate was evaporated in vacuo. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (76 mg, yield 31%).

Workup

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

Sources & evidence

ORD record
ord-ed337e0f78d8477ea8d533f5e87997f6
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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