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

HRID 238001Notes

Reaction equation

HRID 238001 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:4][C:3]=1[O:21]C.B(Br)(Br)Br>C(Cl)Cl>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([OH:21])[CH:4]=3)[C:16]=12

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 249051753-(4-fluoro-3-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 249052805-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluorophenolYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BA62 (3-(4-fluoro-3-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine, 30 mg, 0.10 mmol) was dissolved in CH2Cl2 (5 ml) and stirred under an argon atmosphere. BBr3 (500 uL, 0.5 mol) was added slowly with a syringe, while stirring. The reaction was stirred at room temperature for 3 hours then concentrated in vacuo and purified using silica gel column chromatography [MeOH—CH2Cl2, 2:98] to yield BA62d (23 mg, 44% yield). ESI-MS (M+H)+ m/z calcd 288.1, found 288.1.

Workup

  1. stirringwhile stirring
  2. stirringThe reaction was stirred at room temperature for 3 hours
  3. concentrationthen concentrated in vacuo
  4. custompurified
  5. customto yield BA62d (23 mg, 44% yield)

Sources & evidence

ORD record
ord-2793a64974e0483a886c25f6fda944e0
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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