Dimethylformamide → Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylate

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20](S(C)(=O)=O)C=1.C(=O)([O-])[O-].[K+].[K+].C[N:37](C)C=O>>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([O:1][C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[C:12]([O:14][CH3:15])=[O:13])[N:37]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 11430Potassium Carbonate

HCID 19077292Methyl 6-hydroxyquinoline-5-carboxylate

HCID 190772944,6-Dimethoxy-2-methylsulfonylpyridine

Product 1

HCID 19962792Methyl 6-[(4,6-Dimethoxypyrimidin-2-yl)oxy]quinolin-5-carboxylateYield 89%

Procedure

0.8 g of methyl 6-hydroxyquinolin-5-carboxylate, 0.96 g of 4,6-dimethoxy-2-methylsulfonylpyridine and 0.82 g of potassium carbonate were stirred in 30 ml of N,N-dimethylformamide at 80° C. for 3 hours. The mixture was returned to room temperature, then poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure, was crystallized from a solvent mixture of dichloromethane/isopropyl ether to obtain 1.21 g (yield: 89.0%) of the desired compound. mp: 160°-162° C.