Methyl acetoacetate → HCID 135483641, compound

HRID 1725562Notes

Reaction equation

HRID 1725562 reaction equation
CO[C:3](=[NH:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH2:20][NH2:21].[C:22](OC)(=[O:27])[CH2:23][C:24]([CH3:26])=O>CO.O>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH2:20][N:21]1[C:22](=[O:27])[CH:23]=[C:24]([CH3:26])[N:11]=[C:3]1[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 6433572-(2-Fluorophenyl)ethylamineHCID 13590531026384-76-9

Product 1

HCID 135483641HCID 135483641, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Utilizing the methods described in Example 1 the title compound was prepared from 2-hydroxy-benzimidic acid methyl ester (750 mg, 4.0 mmol), 2-(2-fluoro-phenyl)-ethylamine (520 □l, 4.0 mmol) and methyl acetoacetate (4.0 mL) to provide 140 mg (10%) of 3-[2-(2-fluoro-phenyl)ethyl]-2-(2-hydroxy-phenyl)-6-methyl-3H-pyrimidin-4-one as a white solid after flash chromatography on ODS silica gel eluting with methanol-water (4:7) followed by recrystallization from a large volume of toluene (100 mL).

Sources & evidence

ORD record
ord-f8686c68687d470f98bd979a83046529
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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