Dimethylformamide → HCID 12777823, compound

HRID 2269076Notes

Reaction equation

HRID 2269076 reaction equation
CN(C=O)C.[H-].[Na+].[CH2:8]([SH:11])[CH2:9][CH3:10].[NH2:12][C:13]1[N:21]=[C:20](Cl)[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[Cl-].[Na+].O>[NH2:12][C:13]1[N:21]=[C:20]([S:11][CH2:8][CH2:9][CH3:10])[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 12777823HCID 12777823, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To DMF suspension (50 ml) containing sodium hydride (917 mg, 23 mmol, 60% in mineral oil) were added propanethiol (5.0 ml, 55 mmol) and 6-amino-9-benzyl-2-chloropurine (500 mg, 1.9 mmol) in order. The mixture was stirred under heating at 110° C. for 2.5 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 (505 mg, yield 87%).

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-f85ed50be16d4453b4bc8a96b8c83485
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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