Phosphorus oxychloride → Ethyl 2-chloro-4-methylpyrimidine-5-carboxylate

HRID 1458630Notes

Reaction equation

HRID 1458630 reaction equation
O[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178469852Ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate

Product 1

HCID 21220624Ethyl 2-chloro-4-methylpyrimidine-5-carboxylateYield 27%

Procedure

A solution of ethyl 2-hydroxy-4-methylpyrimidine-5-carboxylate (5 g, 27.5 mmol) and POCl3 (84 g, 550 mmol) was heated at reflux under N2 for 1 h. The reaction was cooled and concentrated. The residue was partitioned between CHCl3 and H2O and the organic layer was dried (Na2SO4), filtered, and concentrated to yield the title compound in a yield of 27% (1.5 g); 1HNMR (CDCl3) δ 9.04 (s, 1H), 4.42 (q, 2H), 2.85 (s, 3H), 1.43 (t, 3H).

Workup

  1. temperatureat reflux under N2 for 1 h
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between CHCl3 and H2O
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-986248a5ba764f69baf697b3a073632e
Source dataset
uspto-grants-1998_12
Patent number
US05852028

Reaction notes

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