Benzyl Bromide → 4-Methyl-6-phenethylpyrimidine

HRID 2103975Notes

Reaction equation

HRID 2103975 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][N:3]=1.C([Li])CCC.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 152574,6-DimethylpyrimidineHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 178306554-Methyl-6-phenethylpyrimidineYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4,6-dimethylpyrimidine (1.08 g, 10 mmol) in THF (40 ml) was added dropwise at −78° C. a solution of n-butyllithium. To the solution was added benzylbromide (1.71 g, 10 mmol). The mixture was warmed up to 0° C. and stirred for 30 minutes. To the reaction mixture was added an aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate, washed with water, dried and concentrated. The obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate). The obtained fraction was concentrated to give 4-methyl-6-phenethylpyrimidine (1.7 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe obtained residue was chromatographed on silica gel (n-hexane-ethyl acetate)
  6. concentrationThe obtained fraction was concentrated

Sources & evidence

ORD record
ord-3c1a31d358414febb65bf4ca424f7e35
Source dataset
uspto-grants-2009_08
Patent number
US07576198B1

Reaction notes

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