Dimethylformamide → 6-Amino-9-benzyl-2-(2-dimethylaminoethyl)thiopurine

HRID 2269150Notes

Reaction equation

[H-].[Na+].CN(C=O)C.[CH3:8][N:9]([CH3:13])[CH2:10][CH2:11][SH: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:12][CH2:11][CH2:10][N:9]([CH3:13])[CH3:8])[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: 100 °C

Procedure

To sodium hydride (600 mg, 15 mmol 60% in mineral oil) were added DMF (10 ml), 2-dimethylaminoethanethiol (1.3 g, 9.2 mmol) and 6-amino-9-benzyl-2-chloropurine (100 mg, 0.39 mmol) in order. The mixture was stirred at 100° C. for 10 hours. After addition of saturated brine the reaction mixture was extracted with chloroform and the organic layer was dried on magnesium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (10% methanol/chloroform) to give the subject compound (24 mg, yield 21%).

Workup

extractionwas extracted with chloroform
customthe organic layer was dried on magnesium sulfate
concentrationconcentrated in vacuo to dryness
customThe residue was purified with silica gel chromatography (10% methanol/chloroform)

Sources & evidence

ORD record: ord-46552ca1f2fd48cfaf54e18dc3c7360d
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329381B1

Reaction notes

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