Dimethylformamide → HCID 18332690, compound

HRID 2269085Notes

Reaction equation

HRID 2269085 reaction equation
CN(C=O)C.[H-].[Na+].[C:8]1([CH3:15])[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.[NH2:16][C:17]1[N:25]=[C:24](Cl)[N:23]=[C:22]2[C:18]=1[N:19]=[CH:20][N:21]2[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>[Cl-].[Na+].O>[NH2:16][C:17]1[N:25]=[C:24]([S:14][C:11]2[CH:12]=[CH:13][C:8]([CH3:15])=[CH:9][CH:10]=2)[N:23]=[C:22]2[C:18]=1[N:19]=[CH:20][N:21]2[CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78114-MethylbenzenethiolHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332690HCID 18332690, compoundYield 93%

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 p-toluenethiol (1.9 g, 15 mmol) and 6-amino-9-benzyl-2-chloropurine (100 mg, 0.39 mmol) in order. The mixture was stirred under heating at 100° C. for 3 hours. Brine was added thereto and the mixture was extracted with chloroform. The organic layer was dried on magnesium sulfate, filtrated 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 (124 mg, yield 93%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltrated
  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-c209290ce9ea4d9fb0de067b3a397dbc
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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