Water → Methyl 2-phenylpyrimidine-5-carboxylate

HRID 219635Notes

Reaction equation

HRID 219635 reaction equation
O.Cl.[C:3]([NH2:11])(=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Na].[CH3:13][O:14][C:15](=[O:24])[C:16]([CH:19](OC)OC)=[CH:17]O.O>CN(C=O)C>[CH3:13][O:14][C:15]([C:16]1[CH:17]=[N:10][C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][CH:19]=1)=[O:24]

Participants

6

Reactant 4

HCID 962Water2×HCID 5360545SodiumHCID 16219042Benzamidine HCl hydrateHCID 591179393,3-Dimethoxy-2-methoxycarbonylpropen-1-ol

Product 1

HCID 11206661Methyl 2-phenylpyrimidine-5-carboxylateYield 74.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzamidine hydrochloride hydrate (2 mmol) in anhydrous DMF (4 mL) is added sodium salt of 2-dimethoxymethyl-3-hydroxy-acrylic acid methyl ester (0.46 g, 2.32 mmol) and the reaction mixture heated at 100° C. under N2 for 1 hour. The reaction is cooled to room temperature and water (15 mL) is added. After addition of water, immediate precipitation of the product is observed. The solids are collected by filtration, washed with water (2.5 mL) and vacuum dried to yield 2-phenyl-pyrimidine-5-carboxylic acid methyl ester (0.32 g, 74%). (see: P. Zhichkin, D. J. Fairfax, S. A. Eisenbeis, Synthesis, 2002, 720-722.)

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. filtrationThe solids are collected by filtration
  3. washwashed with water (2.5 mL) and vacuum
  4. customdried

Sources & evidence

ORD record
ord-2ce903fd898140d1b937271641a88f62
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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