Potassium Phosphate, Tribasic → Methyl 6-methyl-2-phenylpyrimidine-4-carboxylate

HRID 553826Notes

Reaction equation

HRID 553826 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7](Cl)[N:6]=1)=[O:4].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.CC(=O)OCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 2736835Methyl 2-chloro-6-methylpyrimidine-4-carboxylateHCID 22728543Water ethylacetate

Product 1

HCID 58101529Methyl 6-methyl-2-phenylpyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-chloro-6-methyl-pyrimidine-4-carboxylic acid methyl ester (930 mg), phenylboronic acid (610 mg), tetrakis(triphenylphosphine)palladium (265 mg) and potassium phosphate (2.12 g) were dissolved in anhydrous dioxane (25 ml) under argon. The mixture was refluxed overnight and worked up with water/EA. The org. phases were dried (Na2SO4) and evaporated off. Column chromatography (EA/Hept 1/5) offered 875 mg of the desired compound.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. dry with materialphases were dried (Na2SO4)
  3. customevaporated off

Sources & evidence

ORD record
ord-99a308eb50b24b91a6980a55a346e494
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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