2-(Isopropylthio)aniline → N-(2-(isopropylthio)phenyl)-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1500457Notes

Reaction equation

HRID 1500457 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[NH:10][N:11]=[C:12]([CH3:13])[C:3]=12.[CH:14]([S:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20])([CH3:16])[CH3:15]>C(O)(C)C>[CH:14]([S:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH:20][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[NH:10][N:11]=[C:12]([CH3:13])[C:3]=12)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 138527202-(Isopropylthio)anilineHCID 1785034684-Chloro-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178503488N-(2-(isopropylthio)phenyl)-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-3-methyl-6-methylmercaptopyrazolo[3,4-d]pyrimidine (A-3) (1.21 g, 5.63 mmol) and 2-(isopropylthio)aniline (A-4) (1.42 g, 8.50 mmol) in isopropanol (56 mL) was stirred at reflux for 3 h. After cooling down to ambient temperature, TEA (0.78 mL, 5.66 mmol) was added to the mixture, and the solution was again heated to reflux for 0.5 h. After cooling down to ambient temperature, the mixture was filtered to give the title compound (A-5) as white solid (1.30 g, 3.77 mmol). MS-ESI (m/z): 346 (M+H)+.

Workup

  1. temperatureat reflux for 3 h
  2. temperaturethe solution was again heated
  3. temperatureto reflux for 0.5 h
  4. temperatureAfter cooling down to ambient temperature
  5. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-dd303b6baf284962a61fa365e36357c6
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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