Water → 6-(5-methylpyrid-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine
Reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[OH:11][CH:12]1[C:20]2[C:15](=[N:16][CH:17]=[CH:18][N:19]=2)[C:14](=[O:21])[N:13]1[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=1.O>N1C=CC=CC=1>[CH3:28][C:25]1[CH:26]=[CH:27][C:22]([N:13]2[CH:12]([O:11][C:2]([O:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[O:3])[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[C:14]2=[O:21])=[N:23][CH:24]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Phenyl chloroformate (16.4 g.) is run, over the course of 10 minutes, at a temperature of about 20° C., into a suspension of 5-hydroxy-6-(5-methylpyrid-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (8.47 g.) in anhydrous pyridine (110 cc.). The reaction mixture is stirred for 3 hours at a temperature of about 20° C. and is then cooled to a temperature of about 5° C. Water (350 cc.) is then added over the course of 15 minutes. The insoluble product is filtered off, washed with water (4×50 cc.), acetonitrile (2×25 cc.) and diisopropyl ether (2×30 cc.). After drying, 6-(5-methylpyrid-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (11.8 g.), which melts at 176° C., is obtained.
Workup
- temperatureis then cooled to a temperature of about 5° C
- filtrationThe insoluble product is filtered off
- washwashed with water (4×50 cc.), acetonitrile (2×25 cc.) and diisopropyl ether (2×30 cc.)
- customAfter drying
Sources & evidence
- ORD record
- ord-09f2574aae7e4b85a4a3ae31c0072597
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04220646
Reaction notes
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