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

HRID 719470

Reaction equation

HRID 719470 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

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 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%).

Workup

  1. temperatureto reflux for 18 h
  2. concentrationThe solvent was concentrated under reduced pressure
  3. washThe product was eluted
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-4733e5488e6246599b516545e84bc19b
Source dataset
uspto-grants-2006_11
Patent number
US07132426B2

Linked notes

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