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

HRID 1984838Notes

Reaction equation

HRID 1984838 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:14](=O)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:17][CH3:18])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2].O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([O:3][C:4]([C:6]1[N:15]=[C:14]([Cl:21])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:17][CH3:18])[CH:12]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136029329HCID 136029329, compound

Product 1

HCID 22668047Ethyl 4-chloro-6-methoxyquinazoline-2-carboxylate

Conditions

Temperature
100 °C

Procedure

To 6-methoxy-4-oxo-3,4-dihydro-quinazoline-2-carboxylic acid ethyl ester (1.38 g, 5.438 mmol) was added POCl3 (25 mL) and the solution was heated at 100° C. for 1.5 h. The solution was concentrated under reduced pressure and the residue was dissolved in EtOAc and washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure to give 1.22 g of 4-chloro-6-methoxy-quinazoline-2-carboxylic acid ethyl ester.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d9068cc893b14b4dbfc9044749608130
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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