Sodium Bicarbonate → 6-Amino-9-benzyl-8-hydroxy-2-(formylmethylthio)purine

HRID 2269040Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH:13]2OCC[O:14]2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:25])[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>Cl.O1CCCC1>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][CH:13]=[O:14])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:25])[N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 70 °C

Procedure

6-Amino-9-benzyl-2-(1,3-dioxolan-2-yl-methyl)thio-8-hydroxypurine (44 mg, 0.12 mmol) was dissolved in a mixture of 3.3N hydrochloric acid (1 ml) and tetrahydrofuran (4 ml). The solution was stirred at 70° C. for 7 hours and then neutralized with aqueous sodium hydrogen carbonate. After removal of tetrahydrofuran in vacuo, the resulting crystals were filtered, washed with water and repulped in methanol to give the subject compound (17 mg, yield 44%).

Workup

customAfter removal of tetrahydrofuran in vacuo
filtrationthe resulting crystals were filtered
washwashed with water

Sources & evidence

ORD record: ord-add3175bc1fc456280dc6a9e3de5f86c
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329381B1

Reaction notes

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