Sodium Carbonate → HCID 85941943, compound

HRID 968685Notes

Reaction equation

HRID 968685 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.COB([C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1)O.[Cl-].[Li+].[C:25](=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.COCCOC>[CH3:25][O:22][C:20](=[O:21])[C:17]1[CH:16]=[CH:15][C:14]([C:6]2[C:5]([Cl:9])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 433294Lithium ChlorideHCID 669046664-Carboxybenzeneboronic acid methyl ester

Product 1

HCID 85941943HCID 85941943, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In a flask was added 2,4,5-trichloro-pyrimidine (1.3 equivalents, 2.66 g, 14.6 mmol), the commercially available 4-carboxyphenyl boronic acid methyl ester (1.0 equivalent, 2.02 g, 11.2 mmol), tetrakis triphenylphosphine palladium (0.1 equivalent, 1.3 g, 1.12 mmol), lithium chloride (3.0 equivalents, 1.4 g, 33.6 mmol), sodium carbonate (2N, 5 mL) and 1,2-dimethoxyethane (20 mL). The resulting mixture was heat at 80° C. for 24 hours then dissolved in ethyl acetate, washed with hydrochloric acid (1N), brine and dried over sodium sulfate. The crude product was purified by chromatography on silica (ethyl acetate, 10% in hexane) to afford 1.21 g of 4-(2,5-dichloro-pyrimidin-4-yl)-benzoic acid methyl ester as a white solid. The structure was confirmed by 1H NMR.

Workup

  1. washwashed with hydrochloric acid (1N), brine
  2. dry with materialdried over sodium sulfate
  3. customThe crude product was purified by chromatography on silica (ethyl acetate, 10% in hexane)

Sources & evidence

ORD record
ord-4bc1337309f543dda44c57d9443d3c30
Source dataset
uspto-grants-2007_12
Patent number
US07304071B2

Reaction notes

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