Cyanogen Bromide → HCID 178458301, compound

HRID 1460971Notes

Reaction equation

S(O)(O)(=O)=O.[NH2:6][C:7]1[N:8]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:22][CH2:23][CH3:24])[NH:10][C:11](=[O:14])[C:12]=1[NH2:13].[N:25]#[C:26]Br.O.O.O.C([O-])(=O)C.[Na+]>C(O)C>[CH2:22]([O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:9]1[N:8]=[C:7]2[C:12](=[N:13][C:26]([NH2:25])=[N:6]2)[C:11](=[O:14])[N:10]=1)[CH2:23][CH3:24]

Participants

Conditions

Temperature: 65 °C

Procedure

A partial solution of 4,5-diamino-2-(2-propoxyphenyl)-pyrimidin-6-one sulphate (1.1 g), cyanogen bromide (0.33 g), and sodium acetate trihydrate (0.42 g) in 50% aqueous ethanol (44 ml) was stirred at room temperature for 2 hours then allowed to stand overnight. The stirred mixture was then heated in a water bath (temperature 65° C.) for 3 hours, extra cyanogen bromide (0.05 g) added, and the mixture heated for a further 2 hours. The suspension was subjected to partial evaporation under reduced pressure then ammonium hydroxide was added to pH 5. The crude product was collected by filtration and recrystallised from acetonitrile to give the pure title compound, 0.6 g, m.p. 322°-335° C. dec. (after melting ca. 200° C.).

Workup

temperaturethe mixture heated for a further 2 hours
customThe suspension was subjected to partial evaporation under reduced pressure
additionammonium hydroxide was added to pH 5
filtrationThe crude product was collected by filtration
customrecrystallised from acetonitrile

Sources & evidence

ORD record: ord-24a8e788c869404396183c22ff83bde4
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05073559

Reaction notes

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