Potassium Carbonate → HCID 85912885, compound

HRID 1785152Notes

Reaction equation

HRID 1785152 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:14])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:16][CH2:17][CH2:18][CH2:19][Cl:20])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 1357422514-Chloro-6-methoxyquinazolin-7-ol

Product 1

HCID 85912885HCID 85912885, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-chloro-6-methoxyquinazolin-7-ol (0.6 g, 2.86 mmol), 1 bromo 4 chlorobutane (0.63 g, 3.7 mmol), potassium carbonate (1.19 g, 8.6 mmol) and dimethylformamide (10 ml) were heated to 95 C for 1.5 hours. The excess potassium carbonate was filtered off and the reaction evaporated under reduced pressure. The residue was purified by flash chromatography on silica eluting with a mixture of 60-100% dichloromethane in hexane and 30-50% ethyl acetate in hexane to give 4-chloro-7-(4-chlorobutoxy)-6-methoxyquinazoline as a solid (0.4 g, 47%)

Workup

  1. temperaturewere heated to 95 C for 1.5 hours
  2. filtrationThe excess potassium carbonate was filtered off
  3. customthe reaction evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica eluting with a mixture of 60-100% dichloromethane in hexane and 30-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8ad3d9a80e0243b48b38504a2db8568c
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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