Water → 6-(2-Bromobenzyl)-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 1434542Notes

Reaction equation

HRID 1434542 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:13])[N:5]=[CH:4][C:3]=1[C:14]([NH2:16])=[O:15].[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25](OC)=O.[O-]CC.[Na+].O>C(O)C.C(OCC)(=O)C>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]1[NH:16][C:14](=[O:15])[C:3]2[CH:4]=[N:5][N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:13])[C:2]=2[N:1]=1

Participants

7

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 119839075-Amino-1-(o-tolyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1354446946-(2-Bromobenzyl)-1-(2-methylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.0 g (9.25 mmol) of 5-amino-1-(2-methylphenyl)-1H-pyrazole-4-carboxamide (Example 25A) and 9.5 g (41.62 mmol) of methyl (2-bromophenyl)acetate are dissolved in 30 ml of absolute ethanol under argon, and 3.15 g (46.6 mmol) of sodium ethoxide are added. The reaction mixture is heated to a reflux overnight. Cooling to room temperature is followed by hydrolysis with 50 ml of water and subsequent extraction with ethyl acetate (2×50 ml). The combined organic phases are dried over sodium sulphate, and the solvent is distilled off under reduced pressure. The crude product is then purified by column chromatography (silica gel; mobile phase cyclohexane/ethyl acetate, gradient 10:1→1:1). 3.01 g (82% of theory) of the product are obtained.

Workup

  1. temperatureThe reaction mixture is heated to a reflux overnight
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe crude product is then purified by column chromatography (silica gel; mobile phase cyclohexane/ethyl acetate, gradient 10:1→1:1)
  5. custom3.01 g (82% of theory) of the product are obtained

Sources & evidence

ORD record
ord-6d29174d13974a62be816ecc8aece48d
Source dataset
uspto-grants-2009_11
Patent number
US07615558B2

Reaction notes

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