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

HRID 238014Notes

Reaction equation

HRID 238014 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[N:16][C:17]=3[NH2:19])[N:12]([CH:20]([CH3:22])[CH3:21])[N:11]=2)[CH:5]=[C:6]([O:8]C)[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:19][C:17]1[N:16]=[CH:15][N:14]=[C:13]2[N:12]([CH:20]([CH3:22])[CH3:21])[N:11]=[C:10]([C:4]3[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([Br:1])[CH:3]=3)[C:18]=12

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 249051843-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 249051863-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-bromophenolYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-bromo-5-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA85, 0.1 mmol) was dissolved in CH2Cl2 (1 ml) and BBr3 (1 mL, 1 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 35 minutes then concentrated in vacuo and purified using by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA87 (10.7 mg, 31% yield). ESI-MS (M+H)+ m/z calcd 348.0, found 348.0.

Workup

  1. stirringThe reaction was stirred at room temperature for 35 minutes
  2. concentrationthen concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-2020c750935c488187f1182c308e85f9
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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