Dimethylformamide → 6-Amino-9-benzyl-2-pentylthiopurine

HRID 2269080Notes

Reaction equation

CN(C=O)C.[H-].[Na+].[CH2:8]([SH:13])[CH2:9][CH2:10][CH2:11][CH3:12].[NH2:14][C:15]1[N:23]=[C:22](Cl)[N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>[Cl-].[Na+].O>[NH2:14][C:15]1[N:23]=[C:22]([S:13][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To DMF suspension (10 ml) containing sodium hydride (277 mg, 6.9 mmol, 60% in mineral oil) were added 1-pentanethiol (2 ml, 16 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 4 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 in vacuo. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (102 mg, yield 81%).

Workup

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

Sources & evidence

ORD record: ord-e03bb4c5b409436dbfe5dcd3f1993e36
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329381B1

Reaction notes

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