Cyanogen Bromide → HCID 178458301, compound

HRID 1532081Notes

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 about 200° C.). NMR (DMSO-d6; 250 MHz) δ: 0.9 (3H, t) ; 1.6 (2H, m) ; 3.9 (2H, t); 6.8 (2H, s); 6.8 (2H, s); 6.9-7.1 (2H, m); 7.3-7.5 (3H, m).

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-f6d57133e2b34ffd9efb34d7a7f5537d
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06200980B1

Reaction notes

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