Potassium Phosphate, Tribasic → 5-(4-Methoxy-2-methylphenyl)-4,6-dimethylpyrimidine

HRID 69325Notes

Reaction equation

HRID 69325 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[C:5]([CH3:18])[CH:4]=1.Br[C:20]1[C:21]([CH3:27])=[N:22][CH:23]=[N:24][C:25]=1[CH3:26].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:20]2[C:21]([CH3:27])=[N:22][CH:23]=[N:24][C:25]=2[CH3:26])=[C:5]([CH3:18])[CH:4]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 149222215-Bromo-4,6-dimethylpyrimidineHCID 185417152-(4-Methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 867178245-(4-Methoxy-2-methylphenyl)-4,6-dimethylpyrimidine

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (5 g, 6 mmol) was added to a degassed mixture of 2-(4-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 120 mmol), 5-bromo-4,6-dimethylpyrimidine (22.5 g, 120 mmol), and potassium phosphate (76.3 g, 359 mmol) in 1,4-dioxane (300 mL) and water (150 mL). The reaction mixture was heated at reflux for 4 hours, whereupon it was filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: ethyl acetate in petroleum ether) provided the product as a brown solid. Yield: 25 g, 110 mmol, 92%. LCMS m/z 229.3 [M+H+]. 1H NMR (300 MHz, CDCl3) δ 8.95 (s, 1H), 6.94 (d, J=8.2 Hz, 1H), 6.87-6.89 (m, 1H), 6.84 (dd, J=8.3, 2.5 Hz, 1H), 3.86 (s, 3H), 2.21 (s, 6H), 1.99 (s, 3H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours, whereupon it
  3. filtrationwas filtered
  4. concentrationconcentrated in vacuo
  5. customPurification via silica gel chromatography (Gradient: ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-dbe1fe449d204da58b966232c2bf3fa7
Source dataset
uspto-grants-2014_09
Patent number
US08822494B2

Reaction notes

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