Acetic Acid → 1-(2,6-Dichlorophenyl)-6-(4-hydroxybenzyl)-3-isopropyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

HRID 353431Notes

Reaction equation

HRID 353431 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:14])[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[C:3]=1[C:18]([NH2:20])=[O:19].[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](OCC)=O)=[CH:24][CH:23]=1.CC[O-].[Na+].CC(O)=O>CCO>[Cl:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]2[N:1]=[C:29]([CH2:28][C:25]3[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=3)[NH:20][C:18](=[O:19])[C:3]=2[C:4]([CH:15]([CH3:16])[CH3:17])=[N:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 28310Ethyl 4-hydroxyphenylacetateHCID 2723922Sodium ethoxideHCID 185406665-amino-1-(2,6-dichlorophenyl)-3-isopropyl-1H-pyrazole-4-carboxylic acid amide

Product 1

HCID 1357306471-(2,6-Dichlorophenyl)-6-(4-hydroxybenzyl)-3-isopropyl-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-oneYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 5-amino-1-(2,6-dichlorophenyl)-3-isopropyl-1H-pyrazole-4-carboxylic acid amide (5.0 g, 16 mmol) in EtOH (20 mL) was added ethyl 4-hydroxyphenylacetate (8.6 g, 48 mmol) followed by NaOEt (2.66M in EtOH, 36 mL, 96 mmol). The reaction was then heated to reflux for 3 h. The reaction was then cooled to room temp and poured onto 10% aq. HOAc (100 mL). The resulting suspension was then cooled to 0° C. and filtered. The precipitate was then washed with 1:1 MeOH/H2O (100 mL) and 1:1 Et2O/hexane (75 mL). The solid was then dried under vacuum to yield the desired product (5.2 g, 76%).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 3 h
  3. temperatureThe resulting suspension was then cooled to 0° C.
  4. filtrationfiltered
  5. washThe precipitate was then washed with 1:1 MeOH/H2O (100 mL) and 1:1 Et2O/hexane (75 mL)
  6. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-e157c286981c4186b12879a5302bdf9a
Source dataset
uspto-grants-2004_06
Patent number
US06753329B2

Reaction notes

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