Methyl acetoacetate → HCID 135507431, compound

HRID 1725563Notes

Reaction equation

HRID 1725563 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:14]=[C:15]([CH2:19][CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=1.[C:22](OC)(=[O:27])[CH2:23][C:24]([CH3:26])=O>CO.O>[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][N:21]2[C:22](=[O:27])[CH:23]=[C:24]([CH3:26])[N:11]=[C:3]2[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[OH:10])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 5339282-(3-Fluorophenyl)ethanamineHCID 13590531026384-76-9

Product 1

HCID 135507431HCID 135507431, 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 (500 mg, 2.67 mmol), 2-(3-fluoro-phenyl)-ethylamine (330 μl, 2.6 mmol) and methyl acetoacetate (3.0 mL) yielding 160 mg (10%) of 3-[2-(3-fluoro-phenyl)-ethyl]-2-(2-hydroxy-phenyl)-6-methyl-3H-pyrimidin-4-one as a white solid after two purifications by flash chromatography on ODS silica gel eluting with methanol-water (4.5:6.5) followed by recrystallization from a large volume of toluene (100 mL).

Sources & evidence

ORD record
ord-817c0ca281fb4e07acdadc05e29dd8c5
Source dataset
uspto-grants-2009_02
Patent number
US07491728B2

Reaction notes

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