Hydrochloric Acid → 6-(3-Chlorobenzyl)-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 1434540Notes

Reaction equation

HRID 1434540 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])[N:5]=[CH:4][C:3]=1[C:15]([NH2:17])=[O:16].[Cl:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26](OC)=O)[CH:22]=[CH:23][CH:24]=1.[H-].[Na+].Cl>C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[CH2:25][C:26]1[NH:17][C:15](=[O:16])[C:3]2[CH:4]=[N:5][N:6]([C:7]3[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][C:8]=3[CH3:14])[C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2733544Methyl 2-(3-chlorophenyl)acetateHCID 121505615-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide

Product 1

HCID 1361755836-(3-Chlorobenzyl)-1-(2,6-dimethylphenyl)-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.1 g (0.43 mmol) of 5-amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carboxamide (Example 16A) is dissolved under argon in 6 ml of absolute ethanol and 0.24 g (1.3 mmol) of methyl 3-chlorophenylacetate and 0.17 g (4.34 mmol) of 60% sodium hydride (suspension in mineral oil) are added. The reaction mixture is heated to reflux overnight. Cooling to room temperature is followed by acidification with concentrated hydrochloric acid. The sodium chloride precipitated thereby is filtered off. The filtrate is concentrated in vacuo, and the remaining residue 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). 59 mg (37% of theory) of the product are obtained as a colourless solid.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux overnight
  3. customThe sodium chloride precipitated
  4. filtrationthereby is filtered off
  5. concentrationThe filtrate is concentrated in vacuo
  6. customthe remaining residue 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)
  7. custom59 mg (37% of theory) of the product are obtained as a colourless solid

Sources & evidence

ORD record
ord-58bfcd1382804bfca8aa5c9f1e4c8c9e
Source dataset
uspto-grants-2009_11
Patent number
US07615558B2

Reaction notes

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