Boron tribromide → 2-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-4-trifluoromethyl-phenol

HRID 1396550Notes

Reaction equation

HRID 1396550 reaction equation
C[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.B(Br)(Br)Br>C(Cl)Cl>[NH2:22][C:18]1[N:17]=[C:16]2[N:15]([CH3:23])[N:14]=[C:13]([C:4]3[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:3]=3[OH:2])[C:21]2=[CH:20][N:19]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 689621693-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Product 1

HCID 1363872192-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-4-trifluoromethyl-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-Methoxy-5-trifluoromethyl-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Example 88) (0.08 g, 0.25 mmol) in DCM (5 ml) is added drop wise boron tribromide (1M solution in DCM, 0.99 ml, 0.99 mmol), under an inert atmosphere of argon at 0-5° C. (ice-bath). The reaction mixture is warmed to room temperature, stirred for 2 hours and then quenched with water (10 ml). The resulting solid is collected by filtration and dried under vacuum to afford the title compound.

Workup

  1. customat 0-5° C.
  2. customquenched with water (10 ml)
  3. filtrationThe resulting solid is collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b9035cce7b934c8abab5b1c630cd865d
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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