Sodium Nitrite → 7-[(4-Chlorophenyl)methyl]-2,3,6,7-tetrahydro-1H-purine-2,6-dione

HRID 2200618Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-amino-7-(4-chlorobenzyl)-1H-purin-6(7H)-one (6.8 g, 24.7 mmol) in acetic acid (80 mL) and water (10 mL) was added a solution of sodium nitrite (3.4 g, 24.7 mmol) in water (10 mL) dropwise at 50° C. The reaction was stirred at 50° C. for 1 h. The mixture was cooled to room temperature and stirred for another 1.5 h. The precipitate was collected, washed with water and ethanol, and dried in vacuo to give 7-(4-chlorobenzyl)-1H-purine-2,6(3H,7H)-dione (6.5 g, 95.3% yield) as yellow solid. LCMS retention time 0.635 min; LCMS MH+ 277.

Workup

temperatureThe mixture was cooled to room temperature
stirringstirred for another 1.5 h
customThe precipitate was collected
washwashed with water and ethanol
customdried in vacuo

Sources & evidence

ORD record: ord-efd7516beae9434bb36c718b5fed120a
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

Loading…