Boron tribromide → 4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2,5-difluorophenol

HRID 238003Notes

Reaction equation

HRID 238003 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([F:10])=[CH:4][C:3]=1[C:11]1[C:19]2[C:14](=[N:15][CH:16]=[N:17][C:18]=2[NH2:20])[N:13]([CH:21]([CH3:23])[CH3:22])[N:12]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:20][C:18]1[N:17]=[CH:16][N:15]=[C:14]2[N:13]([CH:21]([CH3:23])[CH3:22])[N:12]=[C:11]([C:3]3[C:2]([F:1])=[CH:7][C:6]([OH:8])=[C:5]([F:10])[CH:4]=3)[C:19]=12

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 249051763-(2,5-difluoro-4-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 1359479744-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2,5-difluorophenolYield 36.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2,5-difluoro-4-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA63) (20 mg, 0.06 mmol) was dissolved in CH2Cl2 (2 ml) and BBr3 (0.630 mL, 0.63 mmol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for overnight then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA93 (6.7 mg, 35% yield). ESI-MS (M+H)+ m/z calcd 306.1, found 306.0.

Workup

  1. stirringThe reaction was stirred at room temperature for overnight
  2. concentrationthen concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-f13630d9ac9c48e099722450e156e3db
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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