6-Amino-1-ethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione → 6-Amino-1-ethyl-5-nitroso-1,3-dihydropyrimidine-2,4-dione

HRID 1258029

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-amino-1-ethyl-1,3-dihydropyrimidine-2,4-dione (5.0 g, 32.3 mmol) in a mixture of 50% acetic acid/water (50 ml) at 70° C. was added sodium nitrite (4.45 g, 64.5 mmol) in portions over a period of 30 minutes. The mixture was stirred at 70° C. for a further 30 minutes. The reaction mixture was cooled, and the precipitate filtered off, and washed with water, then methanol, to provide 6-amino-1-ethyl-5-nitroso-1,3-dihydropyrimidine-2,4-dione, a compound of formula (14).

Workup

temperatureThe reaction mixture was cooled
filtrationthe precipitate filtered off
washwashed with water

Sources & evidence

ORD record: ord-01fcf809b2a240d7b412c4a21ace0e5e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466129B2

Linked notes

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