Hydrochloric Acid → HCID 53833316, compound

HRID 861331Notes

Reaction equation

C(O[C:4]([C:6]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:9]=[CH:8][N:7]=1)=[O:5])C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1.Cl>C1COCC1>[CH2:15]([O:14][C:12]([C:11]1[C:6]([C:4]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[O:5])=[N:7][CH:8]=[N:9][CH:10]=1)=[O:13])[CH3:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To a THF solution(30 ml) of pyrimidine-4,5-dicarboxylic acid diethyl ester(1.46 g,6.52 mmol) which was prepared by the method described in the literature(Chem. Pharm. Bull.,1972,20,1513-1521) was added a THF solution of 4-methoxyphenyl magnesium bromide (1.25M,5.47 ml) dropwise at -78° C. The reaction solution was stirred at -78° C. for 30 min, treated with 1N HCl and extracted with AcOEt. The organic layer was washed with brine and dried over MgSO4. After removal of the solvent under reduced pressure the residue was purified by silica gel column chromatography(E. Merck Kieselgel 60/chloroform) to give 4-(4-methoxyphenylcarbonyl)pyrimidine-5-carboxylic acid ethyl ester(1.57 g) as a pale yellow oil.

Workup

extractionextracted with AcOEt
washThe organic layer was washed with brine
dry with materialdried over MgSO4
customAfter removal of the solvent under reduced pressure the residue
customwas purified by silica gel column chromatography(E

Sources & evidence

ORD record: ord-2e71709f0aa74c94a015b4d8d7866596
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05714479

Reaction notes

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