1-Bromo-3-chloropropane → 7-(3-Chloropropoxy)6-methoxyquinazoline

HRID 2182546Notes

Reaction equation

HRID 2182546 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:12][CH3:13].Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:18][CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 1360078727-Hydroxy-6-methoxyquinazoline

Product 1

HCID 867597357-(3-Chloropropoxy)6-methoxyquinazolineYield 85.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 44-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (957 mg, 3 mmol), (prepared as described for the starting material in Example 2), 1-bromo-3-chloropropane (2.36 g, 15 mmol) and potassium carbonate (2.1 g, 15 mmol) in DMF (20 ml) was heated at 40° C. for 1.5 hours. The mixture was allowed to cool, was diluted with water and extracted with ethyl acetate (3×50 ml). The organic extracts were combined, washed with water and brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was triturated with hexane/ethyl acetate, collected by filtration and dried under vacuum to give 4-chloro-2-fluoroanilino)-7-(3-chloropropoxy)6-methoxyquinazoline (650 mg, 55%).

Workup

  1. custom(prepared
  2. temperatureto cool
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation
  7. customThe residue was triturated with hexane/ethyl acetate
  8. filtrationcollected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-dea00874d70b41e69bb7e1884bb05c60
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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