Methanol → HCID 22478229, compound

HRID 2182549Notes

Reaction equation

HRID 2182549 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[Cl:7][C:8]1[CH:31]=[CH:30][C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27]SC)=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:32])[CH:9]=1.[CH3:33]O>O.C(Cl)Cl>[Cl:7][C:8]1[CH:31]=[CH:30][C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][S:3]([CH3:33])(=[O:5])=[O:2])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:32])[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 22478299HCID 22478299, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22478229HCID 22478229, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of OXONE, (trade mark of E.I. du Pont de Nemours & Co., Inc), (652 mg) in water (1.6 ml) was added to a solution of 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methylthioethoxy)quinazoline (200 mg, 0.5 mmol), (prepared as described in Example 29), in methanol (10 ml) and the mixture was stirred for 18 hours at ambient temperature. The mixture was diluted with methylene chloride, was washed with aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvent was removed by evaporation. The residue was triturated with ethyl acetate/hexane, collected by filtration and dried to give 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-methylsulphonylethoxy)quinazoline (172 mg, 80%).

Workup

  1. washwas washed with aqueous sodium hydrogen carbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe residue was triturated with ethyl acetate/hexane
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-38d73c22ef5f4185b562eebe384405eb
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

Loading…