Phosphorus oxychloride → Ethyl 4-chloro-6-fluoroquinazoline-2-carboxylate

HRID 625798Notes

Reaction equation

HRID 625798 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:6][C:5]2=O.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136029321Ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 86649062Ethyl 4-chloro-6-fluoroquinazoline-2-carboxylate

Procedure

A stirred solution of ethyl 6-fluoro-4-oxo-3,4-dihydroquinazoline-2-carboxylate (1.2 g, 5.08 mmol) in phosphorus oxychloride (15 mL) was heated at 105° C. for 6 h. After cooling to rt, the reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in anhydrous toluene. The toluene was concentrated under reduced pressure. The residue was dissolved in a small volume of DCM and it was passed through a short pad of silica gel eluting with DCM. Ethyl 4-chloro-6-fluoroquinazoline-2-carboxylate was obtained as a solid (1.3 g, 100%). LC-MS (ESI) m/z 255 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in anhydrous toluene
  3. concentrationThe toluene was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in a small volume of DCM and it

Sources & evidence

ORD record
ord-c1c37290ddcb4c7e8b32b536379811e3
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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