Potassium Carbonate → HCID 22478201, compound

HRID 1838576Notes

Reaction equation

HRID 1838576 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4]Br.[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:29])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:26][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:29])[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 22478201HCID 22478201, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Bromoacetaldehyde dimethyl acetal (0.74 ml, 3.1 mmol) was added to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (1.0 g, 3.13 mmol), (prepared as described for the starting material in Example 2), and anhydrous potassium carbonate (2.16 g, 15.6 mmol) in DMF (30 ml). The mixture was stirred and heated at 110° C. for 4 hours, then allowed to cool and the volatiles were removed by evaporation. Water was added to the residue and the aqueous mixture was extracted with methylene chloride (×4). The extracts were combined, washed with brine and dried by filtration through phase separating paper. The volatiles were removed by evaporation, the residue was triturated with ether, collected by filtration and dried to give 4-(4-chloro-2-fluoroanilino)-7-(2,2-dimethoxyethoxy)-6-methoxyquinazoline (440 mg, 35%).

Workup

  1. custom(prepared
  2. temperatureto cool
  3. customthe volatiles were removed by evaporation
  4. additionWater was added to the residue
  5. extractionthe aqueous mixture was extracted with methylene chloride (×4)
  6. washwashed with brine
  7. customdried by filtration through phase
  8. customseparating paper
  9. customThe volatiles were removed by evaporation
  10. customthe residue was triturated with ether
  11. filtrationcollected by filtration
  12. customdried

Sources & evidence

ORD record
ord-73f16412ea98445c9f4cd5bd8c581de4
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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