Methanol → HCID 22478229, compound

HRID 1838560Notes

Reaction equation

HRID 1838560 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-9556acdd7d5c4a25a9d71220ea87aa92
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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