Methyl 4-(2-oxo-1,2-dihydropyrimidin-5-yl)benzoate → HCID 54013698, compound

HRID 1264303Notes

Reaction equation

HRID 1264303 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:6][CH:5]=1>CN(C=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][NH:12][C:13](=[O:16])[NH:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 53222356Methyl 4-(2-oxo-1,2-dihydropyrimidin-5-yl)benzoate

Product 1

HCID 54013698HCID 54013698, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-oxo-pyrimidin-5-yl)-benzoic acid methyl ester (761 mg, 3.3 mmol, reference example 19c) in DMF (20 mL) and methanol (5 mL) was added Pd on carbon (250 mg, 10% w/w). The resulting mixtured was stirred under an atmosphere of hydrogen gas for 3 h. This mixture is purged with nitrogen gas then filtered through celite. The filtrate is concentrated and the residue purified by flash chromatography (eluting with 5% methanol in dichloromethane) to give the title compound (421 mg) as a white solid. 1H NMR (CD3OD) ? 3.28 (m, 1H), 3.47 (d, J=7 Hz, 4H), 3.90 (s, 3H), 7.44 (d, J=8 Hz, 2H), 7.90 (d, J=8 Hz, 2H).

Workup

  1. customThis mixture is purged with nitrogen gas
  2. filtrationthen filtered through celite
  3. concentrationThe filtrate is concentrated
  4. customthe residue purified by flash chromatography (eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-adee22ef0a6b4373b57568e5543e2a29
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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