6-Amino-1-ethyl-3-propyl-2,4(1H,3H)-pyrimidinedione → 6-Amino-1-ethyl-5-nitroso-3-propyl-1,3-dihydropyrimidine-2,4-dione

HRID 1246231Notes

Reaction equation

[NH2:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]([CH2:11][CH2:12][CH3:13])[C:4](=[O:14])[CH:3]=1.[N:15]([O-])=[O:16].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]([CH2:11][CH2:12][CH3:13])[C:4](=[O:14])[C:3]=1[N:15]=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-amino-1-ethyl-3-propyl-1,3-dihydropyrimidine-2,4-dione (1.4 g, 7.1 mmol) in a mixture of 50% acetic acid/water (35 ml) was added sodium nitrite (2 g, 28.4 mmol) in portions over a period of 10 minutes. The mixture was stirred at 70° C. for 1 hour, 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-1-ethyl-5-nitroso-3-propyl-1,3-dihydropyrimidine-2,4-dione, a compound of formula (1). MS m/z 227.05 (M+), 249.08 (M++Na)

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-eeac052c3138495daf09dd5c8e840ad9
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125993B2

Reaction notes

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