N,N-Dimethylaniline → 4-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2=[N:17][CH:18]=[N:19][C:20](O)=[C:15]2[CH:14]=[N:13]1.O=P(Cl)(Cl)[Cl:24].CN(C)C1C=CC=CC=1>>[Cl:24][C:20]1[N:19]=[CH:18][N:17]=[C:16]2[N:12]([C:3]3[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=3[F:1])[N:13]=[CH:14][C:15]=12

Participants

Reactant 3

HCID 949N,N-Dimethylaniline

HCID 24813Phosphorus oxychloride

HCID 178504786HCID 178504786, compound

Product 1

HCID 218976614-Chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidineYield 95.2%

Procedure

1-(2-Fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (0.774 g, 2.51 mmol) was suspended in POCl3 (23 mL, 251 mmol) and dimethylaniline (0.69 mL) and the mixture brought to reflux for 18 h. The solvent was concentrated under reduced pressure and the residue loaded to a column of silica gel. The product was eluted using 5% ethyl acetate/dichloromethane. Removal of solvent afforded 4-chloro-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidine as a white solid (0.781 g, 95%). 1H NMR (400 MHz DMSO-d6) δ (ppm): 9.14 (s, 1H); 9.07 (s, 1H); 8.34 (d, 1H); 8.24 (m, 1H); 8.20 (m, 1H); 3.55(s, 3H). Exact mass calculated for C12H8ClFN4O2S 326, found 327.2 (MH+, 100%).