Water → N-(2,4-Dichloropyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamide

HRID 576911Notes

Reaction equation

HRID 576911 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(=O)([O-])O.[Na+].O.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[C:20](Cl)=[O:21]>C(OCC)(=O)C>[Cl:8][C:5]1[N:4]=[C:3]([Cl:9])[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[C:24]([CH3:28])[C:25]([O:26][CH3:27])=[C:17]([CH3:16])[CH:18]=2)=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2577975-Amino-2,4-dichloropyrimidineHCID 516892Sodium BicarbonateHCID 214353833,5-Dimethyl-4-methoxybenzoyl chloride

Product 1

HCID 86675952N-(2,4-Dichloropyrimidin-5-yl)-4-methoxy-3,5-dimethylbenzamideYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.2 g of 5-amino-2,4-dichloro-pyrimidine in 50 ml of ethyl acetate was added to a mixture of 25 ml of a saturated aqueous solution of sodium hydrogencarbonate and 25 ml of water. Then a solution of 4.9 g of 3,5-dimethyl-4-methoxybenzoyl chloride was added at room temperature over a period of 15 min. The mixture was mixed intensively for 4 h. Then the layers were separated and the aqueous layer was extracted twice with ethyl acetate. After drying over sodium sulfate and filtration the solvent was removed in vacuo to give 7.54 g of raw product. The raw product was triturated with 25 ml of isopropanol. After filtration and washing with 10 ml of isopropanol, 2.74 g of the title compound were obtained as a white solid.

Workup

  1. additionThe mixture was mixed intensively for 4 h
  2. customThen the layers were separated
  3. extractionthe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialAfter drying over sodium sulfate and filtration the solvent
  5. customwas removed in vacuo
  6. customto give 7.54 g of raw product
  7. customThe raw product was triturated with 25 ml of isopropanol
  8. filtrationAfter filtration
  9. washwashing with 10 ml of isopropanol

Sources & evidence

ORD record
ord-8444d82d49904dba868f2042bb0d88cc
Source dataset
uspto-grants-2015_05
Patent number
US09040544B2

Reaction notes

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