6-Amino-3-butyl-1,3-dihydropyrimidine-2,4-dione → 5-Nitroso-6-amino-3-butyl-1,3-dihydropyrimidine-2,4-dione
Reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH2:11][CH3:12])[C:4](=[O:13])[CH:3]=1.[N:14]([O-])=[O:15].[Na+]>C(O)(=O)C>[N:14]([C:3]1[C:4](=[O:13])[N:5]([CH2:9][CH2:10][CH2:11][CH3:12])[C:6](=[O:8])[NH:7][C:2]=1[NH2:1])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 6-amino-3-butyl-1,3-dihydropyrimidine-2,4-dione (4.0 g, 21.88 mmol) and aqueous acetic acid (120 ml) was heated at 70° C. until complete solution as attained, and the solution was cooled to 30° C. Sodium nitrite (3 g) was added in small portions while stirring, forming an orange precipitate. The reaction mixture was cooled to 0° C., and the precipitate filtered off, washed with water, and dried under reduced pressure, to provide 5-nitroso-6-amino-3-butyl-1,3-dihydropyrimidine-2,4-dione, which was used in the next reaction with no further purification.
Workup
- temperaturethe solution was cooled to 30° C
- customforming an orange precipitate
- temperatureThe reaction mixture was cooled to 0° C.
- filtrationthe precipitate filtered off
- washwashed with water
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-f03cf83f8bf040a09c64c8dda943cac0
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105665B2
Reaction notes
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