Sodium Nitrite → 7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 2386600Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of 2-amino-7-(2-propen-1-yl)-1,7-dihydro-6H-purin-6-one (40 g, 0.209 mol) in AcOH (900 ml) and water (100 ml) was heated at 55° C. Sodium nitrite (57.74 g, 0.837 mol) in water (100 ml) was added dropwise. Care; toxic fumes. After the addition was complete (approximately 25 minutes) the reaction mixture was allowed to cool to ambient temperature and then concentrated to approximately ⅓ of its original volume. Water (500 ml) was added and the resulting precipitate collected by filtration. The residue was washed with water then dried at 50° C. over P2O5 and under vacuum for 2 hours to give the title compound (17.20 g). The aqueous fraction was concentrated and water added (100 ml). Again the resulting solid was filtered and dried. This gave more of the title compound (2.31 g). Combined product (19.52 g, 49%). m/z 193.2 [MH+].

Workup

additionAfter the addition
custom(approximately 25 minutes)
temperatureto cool to ambient temperature
concentrationconcentrated to approximately ⅓ of its original volume
additionWater (500 ml) was added
filtrationthe resulting precipitate collected by filtration
washThe residue was washed with water
dry with materialthen dried at 50° C. over P2O5 and under vacuum for 2 hours

Sources & evidence

ORD record: ord-d423dde434fe4773b819cf403b01ae53
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268839B2

Reaction notes

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