Phosphorus oxychloride → 6-Bromo-2-chloro-8-methoxyquinazoline

HRID 2079615Notes

Reaction equation

HRID 2079615 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[N:8]=[C:7](O)[N:6]=[CH:5]2.O=P(Cl)(Cl)[Cl:17]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH3:13])[CH:11]=1)[N:8]=[C:7]([Cl:17])[N:6]=[CH:5]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486945HCID 178486945, compound

Product 1

HCID 467382966-Bromo-2-chloro-8-methoxyquinazolineYield 30%

Conditions

Temperature
110 °C

Procedure

A suspension of 6-bromo-8-methoxyquinazolin-2-ol (43.96 mmol) in POCl3 (120 mL) was heated to 110° C. for 30 minutes The mixture was cooled to room temperature, evaporated POCl3 and partitioned between water and dichloromethane. The organic portion was concentrated to give a crude material which was purified by column chromatography (silica gel, eluted with 2% MeOH in dichloromethane) to yield pure material as a yellow solid in 30% yield (3 steps, 3.62 g). ES/MS m/z 272/274 (MH+).

Workup

  1. temperaturewas cooled to room temperature
  2. customevaporated POCl3
  3. custompartitioned between water and dichloromethane
  4. concentrationThe organic portion was concentrated
  5. customto give a crude material which
  6. customwas purified by column chromatography (silica gel, eluted with 2% MeOH in dichloromethane)
  7. customto yield pure material as a yellow solid in 30% yield (3 steps, 3.62 g)

Sources & evidence

ORD record
ord-fb58a1ccdfa7491aad9cb2d964f5e21c
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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