Water → Carbonic acid, 6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo(3,4-b)pyrazin-5-yl phenyl ester

HRID 27076

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH:26]([OH:27])[C:25]3[C:20](=[N:21][CH:22]=[CH:23][N:24]=3)[C:19]2=[O:28])=[N:16][CH:17]=1.O>N1C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH:19]([O:28][C:2]([O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:3])[C:20]3[C:25](=[N:24][CH:23]=[CH:22][N:21]=3)[C:26]2=[O:27])=[N:16][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Phenyl chloroformate (141 g.) is added, with stirring and whilst keeping the temperature at about 5° C., to a suspension of 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (158 g.) in anhydrous pyridine (1,580 cc.). When the addition is complete, the reaction mixture is heated to a temperature of about 60° C. The heating is continued for one hour. Water (4,750 cc.) is added to the reaction mixture after it has been cooled to a temperature of about 20° C. The product which crystallises is filtered off and washed with water (2×250 cc.), acetonitrile (150 cc.) and diisopropyl ether (250 cc.). After drying, 6-(5-chloropyrid-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]-pyrazine (169 g.), which melts at 193° C., is obtained.

Workup

customat about 5° C.
additionWhen the addition
temperaturehas been cooled to a temperature of about 20° C
customThe product which crystallises
filtrationis filtered off
washwashed with water (2×250 cc.), acetonitrile (150 cc.) and diisopropyl ether (250 cc.)
customAfter drying

Sources & evidence

ORD record: ord-95d29305123c4072a7cdcfc81f025493
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220646

Linked notes

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