Dimethylformamide → HCID 18332711, compound

HRID 2269079Notes

Reaction equation

HRID 2269079 reaction equation
CN(C=O)C.O.[Na].[CH3:8][CH:9]([SH:12])[CH2:10][CH3:11].[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:12][CH:9]([CH2:10][CH3:11])[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 105602-ButanethiolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 71353970Sodium monohydrate

Product 1

HCID 18332711HCID 18332711, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To DMF suspension (10 ml) containing sodium hydrate (300 mg, 7.5 mmol, 60%in mineral oil) were added 2-butanethiol (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 (85 mg, yield 35%).

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-b2440b0e7e954b089bbb58c6a09f680a
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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