Chloral Hydrate → 2-(2-Propoxyphenyl)pteridin-4,6(3H,5H)-dione

HRID 1936682Notes

Reaction equation

Cl[C:2](Cl)(Cl)[CH:3](O)[OH:4].S(O)(O)(=O)=O.[NH2:13][C:14]1[N:15]=[C:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH2:29][CH2:30][CH3:31])[NH:17][C:18](=[O:21])[C:19]=1[NH2:20]>C=O.CO>[CH2:29]([O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:16]1[NH:17][C:18](=[O:21])[C:19]2[NH:20][C:3](=[O:4])[CH:2]=[N:13][C:14]=2[N:15]=1)[CH2:30][CH3:31]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of chloral hydrate (1.74 g) in 50% aqueous methanal (10 ml) was added over 10 minutes to a stirred solution of 4,5-diamino-2-(2-propoxyphenyl)pyrimidin-6-one sulphate (1.89 g) in 50% aqueous methanol (60 ml) at 80° C. and the reaction mixture was stirred at 80° C. for 1.5 hours. The cooled reaction mixture was filtered to remove an orange brown solid which was discarded. On standing overnight the filtrate afforded a crude solid product (0.96 g) which was collected and washed with dilute aqueous potassium bicarbonate and water. The crude product together with another sample (0.20 g) similarly prepared was eluted from a silica column with chloroform. The combined fractions containing product were evaporated under reduced pressure to afford a solid (0.54 g) which was recrystallized from acetonitrile to afford the title compound, 0.39 g, m.p. 232-233.5° C.

Workup

customThe cooled reaction mixture
filtrationwas filtered
customto remove an orange brown solid which
waitOn standing overnight

Sources & evidence

ORD record: ord-bb138f7e0e6d4bbc9a784619c7bd17c9
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391885B1

Reaction notes

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