Potassium Hydroxide → HCID 13589546, compound

HRID 2073623Notes

Reaction equation

[OH-].[K+].[CH2:3]([O:5][C:6]([C:8]1[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[N:12]2[CH:23]=[N:24][C:25]([C:26]([O:28]CC)=[O:27])=[C:11]2[NH:10][C:9]=1[CH3:31])=[O:7])[CH3:4]>O.C(O)C>[C:26]([C:25]1[N:24]=[CH:23][N:12]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=3)[C:8]([C:6]([O:5][CH2:3][CH3:4])=[O:7])=[C:9]([CH3:31])[NH:10][C:11]=12)([OH:28])=[O:27]

Participants

Conditions

Temperature: 70 °C

Procedure

0.17 g of potassium hydroxide in 1.7 ml of water is added to a solution of 1.0 g of 3,8-diethoxycarbonyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydroimidazo[1,5-a]pyrimidine in 20 ml of ethanol, and gradually heated followed by stirring at 70° C. for 10 hours. The ethanol is distilled off under reduced pressure, chloroform is added to the resulting oil and extracted with potassium carbonate solution. The water layer is washed with chloroform and adjusted to pH 5-6 with acetic acid. The precipitated crystals are collected by filtration and recrystallized from ethanol to give 0.32 g of 8-carboxy-3-ethoxycarbonyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydroimidazo[1,5-a]pyrimidine, melting at 222° C. with decomposition.

Workup

temperaturegradually heated
distillationThe ethanol is distilled off under reduced pressure, chloroform
additionis added to the resulting oil
extractionextracted with potassium carbonate solution
washThe water layer is washed with chloroform
filtrationThe precipitated crystals are collected by filtration
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-15f702cf095640dc8f26a98744dc7496
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04918074

Reaction notes

Loading…