Boron tribromide → HCID 135502651, compound

HRID 68934Notes

Reaction equation

HRID 68934 reaction equation
B(Br)(Br)Br.[CH:5]1([CH2:10][C:11]2[NH:12][C:13](=[O:29])[C:14]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26]CC)[C:15]=3[N:16]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1>ClCCl>[CH:5]1([CH2:10][C:11]2[NH:12][C:13](=[O:29])[C:14]3[CH:19]=[N:18][N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[OH:26])[C:15]=3[N:16]=2)[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 135519358HCID 135519358, compound

Product 1

HCID 135502651HCID 135502651, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 ml of 1 M boron tribromide solution in dichloromethane are added to 0.2 g (0.59 mmol) of 6-cyclopentylmethyl-1-(2-ethoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 12), and the reaction mixture was stirred at room temperature for 1 h. Aqueous hydrolysis is followed by extraction with dichloromethane. The product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 0.167 g (91% of theory) of the product is obtained as a colourless solid.

Workup

  1. customAqueous hydrolysis
  2. extractionis followed by extraction with dichloromethane
  3. customThe product is purified by preparative HPLC (YMC Gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  4. custom0.167 g (91% of theory) of the product is obtained as a colourless solid

Sources & evidence

ORD record
ord-97d28992906c483583e673bfda116c1e
Source dataset
uspto-grants-2014_09
Patent number
US08822479B2

Reaction notes

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