Water → 2-Pyridin-3-yl-pyrimidine-5-carboxylic acid methyl ester

HRID 219641

Reaction equation

HRID 219641 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[Na].[CH3:12][O:13][C:14](=[O:23])[C:15]([CH:18](OC)OC)=[CH:16]O.O>CN(C=O)C>[CH3:12][O:13][C:14]([C:15]1[CH:16]=[N:9][C:2]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[N:10][CH:18]=1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 202042Nicotinamidine hydrochlorideHCID 5360545SodiumHCID 591179393,3-Dimethoxy-2-methoxycarbonylpropen-1-ol

Product 1

HCID 685565272-Pyridin-3-yl-pyrimidine-5-carboxylic acid methyl esterYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of nicotinamidine hydrochloride (1 g, 6.35 mmol) in anhydrous DMF (12 mL) is added sodium salt of 2-dimethoxymethyl-3-hydroxy-acrylic acid methyl ester (1.46 g, 7.36 mmol) and the reaction mixture is heated at 100° C. under N2 for 3 hours. After this time the reaction is cooled to room temperature and water (48 mL) is added. The precipitate is collected by filtration, washed with water and vacuum dried to afford 2-pyridin-3-yl-pyrimidine-5-carboxylic acid methyl ester (0.7 g, 51%). MS: 216 (M+H).

Workup

  1. temperatureAfter this time the reaction is cooled to room temperature
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water and vacuum
  4. customdried

Sources & evidence

ORD record
ord-589daa2ddd0e4a7bb46476bd0c62144d
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Linked notes

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