Sodium Nitrite → 7-Benzyl-1H-purine-2,6(3H,7H)-dione

HRID 1792044Notes

Reaction equation

Cl.N[C:3]1[NH:4][C:5](=[O:19])[C:6]2[N:7]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]=[N:9][C:10]=2[N:11]=1.N([O-])=[O:21].[Na+]>C(O)(=O)C.O>[CH2:12]([N:7]1[C:6]2[C:5](=[O:19])[NH:4][C:3](=[O:21])[NH:11][C:10]=2[N:9]=[CH:8]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A white suspension of 2-amino-7-benzyl-1,7-dihydropurin-6-one hydrochloride (12.88 g) in acetic acid (320 ml) and water (32 ml) was stirred at 110° C. for 10 minutes, and then at 50° C. for 10 minutes. Aqueous solution (32 ml) of sodium nitrite (12.88 g) was slowly added dropwise at 50° C. thereto. The reaction mixture was stirred at 50° C. for 15 hours, and the resulting pale brown suspension was collected by filtration to give 4.27 g of the title compound.

Workup

waitat 50° C. for 10 minutes
stirringThe reaction mixture was stirred at 50° C. for 15 hours
filtrationthe resulting pale brown suspension was collected by filtration

Sources & evidence

ORD record: ord-ed9edb7aaaa148d6b71ad67af5327a84
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074798B2

Reaction notes

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