Potassium Carbonate → 2-[(3-Methyl-4-nitrophenoxy)methyl]pyrimidine

HRID 402691Notes

Reaction equation

HRID 402691 reaction equation
[N+:1]([C:4]1[C:5]([CH3:11])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.Cl[CH2:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[O:10][CH2:14][C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 174123-Methyl-4-nitrophenolHCID 200256062-(Chloromethyl)pyrimidine hydrochloride

Product 1

HCID 867083912-[(3-Methyl-4-nitrophenoxy)methyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-nitro-m-cresol (0.25 g, 1.6 mmol), 2-(chloromethyl)pyrimidine hydrochloride (0.40 g, 2.4 mmol) and potassium carbonate (0.50 g, 4.0 mmol) in N,N-dimethylformamide (6.0 mL) was stirred at 70° C. for 18 h. Cooled to ambient temperature, the reaction mixture was poured into ice water, extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford 2-[(3-methyl-4-nitrophenoxy)methyl]pyrimidine as crude material (0.32 g, y. 81%) as solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c56424a77c214b8ea3f509cf6f206d72
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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