Cysteamine → 6-Amino-9-benzyl-2-(2-aminoethyl)thiopurine

HRID 2269149Notes

Reaction equation

[H-].[Na+].CN(C=O)C.[NH2:8][CH2:9][CH2:10][SH:11].[NH2:12][C:13]1[N:21]=[C:20](Cl)[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[Cl-].[Na+].O>[NH2:12][C:13]1[N:21]=[C:20]([S:11][CH2:10][CH2:9][NH2:8])[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To sodium hydride (300 mg, 7.5 mmol, 60% in mineral oil) were added DMF (10 ml), 2-aminoethanethiol (620 mg, 8 mmol) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred at 100° C. for 3 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 (126 mg, yield 54%).

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-df7b30b7cec841999480b710a9ae013a
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329381B1

Reaction notes

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