Sodium Dithionite → 5,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione

HRID 858037Notes

Reaction equation

[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:4](=[O:17])[C:3]=1[N:18]=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[NH2:18][C:3]1[C:4](=[O:17])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:6](=[O:8])[NH:7][C:2]=1[NH2:1]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-amino-3-(2-fluoro-benzyl)-5-nitroso-1H-pyrimidine-2,4-dione in water at 80° C. was treated with sodium hydrosulfite (5.94 g, 34.16 mmol). The reaction was stirred at 80° C. for 30 min. At this time, the reaction mixture was cooled to 0° C. for 10 min. The resulting solids were collected by filtration, rinsed with cold water and cold ether, and dried in vacuo to afford 5,6-diamino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione (2.34 g, 96%); LRMS for C11H11FN4O2 (M+H)+ at m/z=251.

Workup

temperatureAt this time, the reaction mixture was cooled to 0° C. for 10 min
filtrationThe resulting solids were collected by filtration
washrinsed with cold water and cold ether
customdried in vacuo

Sources & evidence

ORD record: ord-1e38e95761c7457e8c7c4934145fce33
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148229B2

Reaction notes

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