Sodium ethoxide → HCID 178425046, compound

HRID 411587Notes

Reaction equation

HRID 411587 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[Cl:14])[N:5]=[C:4]([CH:15]([CH3:17])[CH3:16])[C:3]=1[C:18]([NH2:20])=[O:19].[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O-])=O)=[CH:24][CH:23]=1.[O-]CC.[Na+]>C(O)C>[Cl:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([CH3:13])[C:7]=1[N:6]1[C:2]2=[N:1][C:29]([CH2:28][C:25]3[CH:26]=[CH:27][C:22]([NH2:21])=[CH:23][CH:24]=3)=[N:20][C:18](=[O:19])[C:3]2=[C:4]([CH:15]([CH3:17])[CH3:16])[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 6930723HCID 6930723, compoundHCID 18540656HCID 18540656, compound

Product 1

HCID 178425046HCID 178425046, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Part D: To a stirred solution of 1.4 g (4.8 mmol) 5-amino-3-isopropyl-1-(2-chloro-6-methyl-phenyl)pyrazole-4-carboxamide in 100 mL absolute ethanol was added 5.14 g (28.8 mmol) of 4-amino-phenylacetate followed by 10.7 mL (28.8 mmol) of 2.66 M sodium ethoxide in ethanol. The solution was stirred 18 h at reflux and the heating mantle was then removed. The reaction was treated with water and 10% aq. HOAc, cooled to ambient temperature, and filtered. The solid purified by coloumn chromatography on silica gel using 1:1 hexanes-EtOAc as eluant to afford 743 mg (38%) of 1-(2-chloro-6-methylphenyl)-3-isopropyl-6-(4-aminobenzyl)-pyrazolo[3,4-d]pyrimidin-4-one, mp 206-207° C. Mass Spec.(CI+): 408 (M+H)+.

Workup

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with water and 10% aq. HOAc
  4. filtrationfiltered
  5. customThe solid purified by coloumn chromatography on silica gel using 1:1 hexanes-EtOAc as eluant

Sources & evidence

ORD record
ord-6b849d4dd35e474f9e7dc7486baed27a
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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