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

HRID 237969Notes

Reaction equation

HRID 237969 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:27]([CH3:29])[CH3:28])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[C:13]([O:25]C)[CH:12]=3)[C:3]=12.B(Br)(Br)Br>C(Cl)Cl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:4](=[N:5][CH:6]=[N:7][C:2]=3[NH2:1])[N:8]([CH:27]([CH3:28])[CH3:29])[N:9]=2)=[CH:12][C:13]=1[OH:25]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 24905150HCID 24905150, compound

Product 1

HCID 249052522-Amino-5-[4-amino-1-(1-methylethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BA20 (tert-butyl 4-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-methoxyphenylcarbamate, 7 mg, 0.018 mmol) was dissolved in CH2Cl2 (2.5 ml) and stirred under an argon atmosphere at room temperature. BBr3 (0.500 ml) was added slowly with a syringe. The reaction mixture was stirred overnight, under argon at room temperature. BBr3 was removed in vacuo and the remaining solid was purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA20dd.

Workup

  1. stirringThe reaction mixture was stirred overnight, under argon at room temperature
  2. customBBr3 was removed in vacuo
  3. customthe remaining solid was purified by RP-HPLC (MeCN:H2O:0.1% TFA)
  4. customto yield BA20dd

Sources & evidence

ORD record
ord-22fd9e1a271e40aa8ee3f24f7348c379
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

Loading…