N,N-Diethylaniline → 4-Chloro-6-methoxy-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidine
Reaction equation
O[C:2]1[N:7]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[NH:5][C:4]([O:18][CH3:19])(O)[CH:3]=1.C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:33]>>[Cl:33][C:2]1[CH:3]=[C:4]([O:18][CH3:19])[N:5]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:12]=2)[N:7]=1Participants
4
Conditions
- Temperature
- 110 °C
Procedure
To a stirred solution of compound 289 (2.38 g, 1 eq.) in POCl3 (7.2 mL) was added N,N-diethylaniline (2.17 g, 1.7 eq.). The mixture was stirred at 110° C. for 16 hrs. The reaction was cooled down to room temperature and poured dropwise into an ice/water mixture. The aqueous solution was extracted with DCM. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by silica gel chromatography to yield compound 290 as an orange solid in 45% yield. MS (ESI, EI+): m/z=296 (MH+).