Phosphorus oxychloride → Ethyl 6-chloro-5-methylpyrimidine-4-carboxylate

HRID 1753220Notes

Reaction equation

HRID 1753220 reaction equation
O[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]=1[CH3:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178470300HCID 178470300, compound

Product 1

HCID 56592992Ethyl 6-chloro-5-methylpyrimidine-4-carboxylate

Conditions

Temperature
100 °C

Procedure

A solution of ethyl 6-hydroxy-5-methylpyrimidine-4-carboxylate 40 (100 g, 549 mmol) in POCl3 (1000 ml) was heated to reflux for 5 h at 100° C. in sealed tube. After cooling to RT, the excess POCl3 was removed under reduced pressure, then quenched with ice water and extracted with EtOAc. The combined organic phase is washed with water, brine and concentrated under reduced pressure to afford ethyl 6-chloro-5-methylpyrimidine-4-carboxylate 41 as a black liquid. Yield: 80 (72%). This material was used as such for next step without purification.

Workup

  1. temperatureAfter cooling to RT
  2. customthe excess POCl3 was removed under reduced pressure
  3. customquenched with ice water
  4. extractionextracted with EtOAc
  5. washThe combined organic phase is washed with water, brine
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6f644e9afd3433c80f6bda4a43b289e
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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