6-Amino-3-propylpyrimidine-2,4(1H,3H)-dione → 6-Amino-5-nitroso-3-propylpyrimidine-2,4(1H,3H)-dione
Reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[CH:3]=1.[N:13]([O-])=[O:14].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[N:13]=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 6-amino-3-propyl-1,3-dihydropyrimidine-2,4-dione (5.6 g) in a mixture of 50% acetic acid/water (160 ml) at 70° C. was added sodium nitrite (4.5 g) in portions over a period of 15 minutes. The mixture was stirred at 70° C. for 45 minutes, then the reaction mixture concentrated to a low volume under reduced pressure. The solid was filtered off, and washed with water, to provide 6-amino-5-nitroso-3-propyl-1,3-dihydropyrimidine-2,4-dione, a compound of formula (11).
Workup
- concentrationthe reaction mixture concentrated to a low volume under reduced pressure
- filtrationThe solid was filtered off
- washwashed with water
Sources & evidence
- ORD record
- ord-e1fb277962214ae1a51b984f64b509d1
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609671B2
Reaction notes
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