Dimethylformamide → N-Methyl-(6-amino-9-benzyl-2-purinyl)thioacetamide

HRID 2269154Notes

Reaction equation

[H-].[Na+].C[N:4]([CH:6]=O)C.[SH:8]CC(NC)=O.[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.CCCC[CH2:36][CH3:37]>[Cl-].[Na+].O>[CH3:6][NH:4][C:36](=[S:8])[CH2:37][C:22]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:15]([NH2:14])[N:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium hydride (320 mg, 8 mmol 60% in mineral oil) was washed with hexane. Thereto were added DMF (10 ml), 2-mercapto-N-methylacetamide (1 ml) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred at 100° C. for 8 hours. After addition of saturated brine the reaction mixture was extracted with ethyl acetate. The organic layer was dried on magnesium sulfate and the solvent was removed in vacuo. The residue was purified with silica gel chromatography (3% methanol/chloroform) to give the subject compound (158 mg, yield 60%).

Workup

extractionwas extracted with ethyl acetate
customThe organic layer was dried on magnesium sulfate
customthe solvent was removed in vacuo
customThe residue was purified with silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record: ord-ecefc0547f484b0b8b6865d2ce4f6a7e
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329381B1

Reaction notes

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