Phosphorus oxychloride → 2-Chloro-6-methoxyquinazoline

HRID 639354Notes

Reaction equation

HRID 639354 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8](O)[N:7]=[CH:6]2.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:8]1[N:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488027HCID 178488027, compound

Product 1

HCID 592548522-Chloro-6-methoxyquinazolineYield 90%

Procedure

6-methoxyquinazolin-2-ol (1eq) and phosphorus oxychloride (2-10eq) was refluxed for 2 hours. The reaction mixture was concentrated and neutralized with sodium carbonate, which was then filtered off. The concentrate was partitioned between ethyl acetate and water. The organic layer was then washed with brine dried and concentrated. The crude was subjected to column chromatography (10% Acetone in hexane) to afford 2-chloro-6-methoxyquinazoline as a beige color solid in 90% yield.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationwas then filtered off
  3. customThe concentrate was partitioned between ethyl acetate and water
  4. washThe organic layer was then washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-47bd76c8e845491bb1fa6d0fb243495c
Source dataset
uspto-grants-2010_04
Patent number
US07691866B2

Reaction notes

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