Trichloroisocyanuric Acid → 3-(3-Chloro-2-methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

HRID 1396564Notes

Reaction equation

HRID 1396564 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[C:21]2[C:16](=[N:17][C:18]([NH2:22])=[N:19][CH:20]=2)[N:15]([CH3:23])[N:14]=1.[Cl:24]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>S(=O)(=O)(O)O>[Cl:24][C:8]1[C:3]([O:2][CH3:1])=[C:4]([C:13]2[C:21]3[C:16](=[N:17][C:18]([NH2:22])=[N:19][CH:20]=3)[N:15]([CH3:23])[N:14]=2)[CH:5]=[C:6]([C:9]([F:11])([F:12])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 689621693-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Product 1

HCID 689660943-(3-Chloro-2-methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

3-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Example 88) (526 mg, 1.62 mmol) is dissolved in concentrated sulfuric acid (98%, 15 ml) and trichloroisocyanuric acid (126 mg, 0.54 mmol) is added. The reaction mixture is stirred at room temperature for 3 days, poured onto ice water (100 ml) and stirred for 30 minutes. The resulting precipitate is collected by filtration and dried under vacuum to afford the title compound as the sulfate salt.

Workup

  1. additionpoured onto ice water (100 ml)
  2. stirringstirred for 30 minutes
  3. filtrationThe resulting precipitate is collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e53a1911da264b358f8324730c77ff63
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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