Sodium Dithionite → 5,6-Diamino-1-(2-furanylmethyl)-2,4(1H,3H)-pyrimidinedione

HRID 1421237Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

6-Amino-1-furfuryluracil (3.0 g, 14.5-mmol) was dissolved with heating in 30% aqueous acetic acid (30 ml) and then a solution of sodium nitrite (1.7 g, 24.6 mmol) in water (5 ml) was added dropwise. The reaction was heated to 70° C. for 30 min and then cooled to 0° C. The solids were collected by filtration and rinsed with cold water (20 ml). The solids were dissolved into concentrated aqueous ammonium hydroxide solution (10 ml) and then a solution of sodium hydrosulfite (9.8 g, 47.8 mmol) in water (30 ml) was added in one portion. After heating at 80° C. for 1 hour, the slurry was cooled to ambient temperature. The solids were collected by filtration, rinsed with water (4×50 ml) and vacuum dried over phosphorus pentoxide to give 5,6-diamino-1-furfuryluracil (1.72 g, 53% yield) as a brown solid.

Workup

temperaturecooled to 0° C
filtrationThe solids were collected by filtration
washrinsed with cold water (20 ml)
dissolutionThe solids were dissolved into concentrated aqueous ammonium hydroxide solution (10 ml)
temperatureAfter heating at 80° C. for 1 hour
temperaturethe slurry was cooled to ambient temperature
filtrationThe solids were collected by filtration
washrinsed with water (4×50 ml) and vacuum
dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record: ord-67bf09500f834f5c80ad157b71d1fa85
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06075029

Reaction notes

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