4,6-Dichloro-5-(2-methoxyphenoxy)pyrimidine → 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]-2-pyridine sulfonamide
Reaktionsgleichung
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=1.[K+].[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH-:31])(=[O:30])=[O:29])=[N:26][CH:27]=1)([CH3:21])[CH3:20]>CN(C=O)C>[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:31][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=2)(=[O:30])=[O:29])=[N:26][CH:27]=1)([CH3:21])[CH3:20]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 2.71 g of 4,6-dichloro-5-(o-methoxyphenoxy)-pyrimidine (Example 10b) and 5.0 g of 5-isopropyl pyridine-2-sulfonamide potassium salt (Example 1e) in 50 ml of DMF was stirred at room temperature for 20 h. The solvent was removed in vacuo, the residue was taken up in 200 ml of 10% aqueous acetic acid and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated. The crude product was crysallised from a mixture of 2-propanol and diethyl ether. The crystals were collected, washed with cold 2-propanol and diethyl ether and dried to give 2.8 g of 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]-2-pyridine sulfonamide as white crystals. LC-MS: tR=4.99 min, [M+1]+=435.25, [M−1]−=433.28.