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

HRID 1458630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1458630
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

Komponenten

3

Edukt 2

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-986248a5ba764f69baf697b3a073632e
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05852028

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