Water → Methyl 2-(pyridin-4-yl)pyrimidine-5-carboxylate

HRID 219638

Reaction equation

HRID 219638 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH: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:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[N:10][CH:18]=1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 2776844Pyridine-4-amidine hydrochlorideHCID 5360545SodiumHCID 591179393,3-Dimethoxy-2-methoxycarbonylpropen-1-ol

Product 1

HCID 69122655Methyl 2-(pyridin-4-yl)pyrimidine-5-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of isonicotinamidine 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 nitrogen for 1 h. 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-4-yl-pyrimidine-5-carboxylic acid methyl ester (1.2 g, 88%). MS: 216 (M+H); 1H NMR (300 MHz, CD3OD): δ 4.00 (s, 3H), 8.44 (d, 2H), 8.73 (d, 2H), 9.38 (s, 2H).

Workup

  1. temperatureThe 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-9dc033b50dac4503bb2dff46aff4e7db
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Linked notes

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