Phosphorus oxychloride → HCID 86647813, compound

HRID 241007Notes

Reaction equation

HRID 241007 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:8](O)=[N:9][C:10]([CH3:14])=[N:11][C:12]=2[CH3:13])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:8]1[C:7]([CH2:6][C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)=[C:12]([CH3:13])[N:11]=[C:10]([CH3:14])[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178432729HCID 178432729, compound

Product 1

HCID 86647813HCID 86647813, compoundYield 67%

Procedure

A solution of 5-(4-fluorobenzyl)-2,6-dimethylpyrimidin-4-ol (730 mg, 3.14 mmol) in phosphorus oxychloride (10 mL) was stirred at 60° C. for 90 min. The reaction mixture was concentrated and ethyl acetate (50 mL) was added to the residue. The organic solution was washed with saturated sodium bicarbonate (50 mL), water (50 mL), and brine (50 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography of the residue on silica (5-40% ethyl acetate in hexanes) afforded 4-chloro-5-(4-fluorobenzyl)-2,6-dimethylpyrimidine (527 mg, 67% yield) as a colorless solid. 1H NMR (400 MHz, CDCl3): 7.21 (m, 2H), 6.98 (m, 2H), 4.12 (s, 2H), 2.67 (s, 3H), 2.45 (s, 3H); MS (EI) for C13H12ClFN2: 250 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionethyl acetate (50 mL) was added to the residue
  3. washThe organic solution was washed with saturated sodium bicarbonate (50 mL), water (50 mL), and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a9cccbf431654df6862952f2d7a6bc9a
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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