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

HRID 1958364Notes

Reaction equation

HRID 1958364 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3=[N:16][CH:17]=[N:18][C:19](O)=[C:14]3[CH:13]=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:32]>>[Cl:32][C:19]1[N:18]=[CH:17][N:16]=[C:15]2[N:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[N:12]=[CH:13][C:14]=12

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178504785HCID 178504785, compound

Product 1

HCID 218974474-Chloro-1-[4-(methanesulfonyl)phenyl]-1H-pyrazolo[3,4-d]pyrimidineYield 27%

Procedure

Into a 50 mL round-bottomed equipped with a reflux condenser and N2 inlet septum was place a stir bar, 1-(4-methanesulfonyl-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (93 mg, 0.32 mmol), dimethylaniline (0.3 mL) and POCl3 (10 mL). The reaction mixture was stirred at room temperature under N2 for 5 minutes and brought to reflux for 6 hrs. After cooling down to room temperature, the reaction mixture was poured into ice and extracted with CH2Cl2 quickly. The crude product was then purified by flash chromatography (EtOAc:Hex=1:1), 24 mg of product was obtained (27% yield). 1H NMR (DMSO-d6, 400 MHz) δ 3.29 (s, 3H), 8.19 (d, 2H), 8.53 (d, 2H), 8.89 (s, 1H), 9.08 (s, 1H). LCMS calculated C12H9ClN4O2S 308.01, observed 309.1 (MH+).

Workup

  1. customInto a 50 mL round-bottomed equipped with a reflux condenser and N2 inlet septum
  2. temperatureto reflux for 6 hrs
  3. temperatureAfter cooling down to room temperature
  4. additionthe reaction mixture was poured into ice
  5. extractionextracted with CH2Cl2 quickly
  6. customThe crude product was then purified by flash chromatography (EtOAc:Hex=1:1)

Sources & evidence

ORD record
ord-1d44b55a8fc34c32b8db305c980d8ab6
Source dataset
uspto-grants-2013_04
Patent number
US08410119B2

Reaction notes

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