Sodium ethoxide → HCID 178490012, compound

HRID 411570Notes

Reaction equation

HRID 411570 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[C:4]([CH:16]([CH3:18])[CH3:17])[C:3]=1[C:19]([NH2:21])=[O:20].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31](Cl)=O)[CH:27]=[CH:28][CH:29]=1.[O-]CC.[Na+]>C(O)C>[Cl:13][C:12]1[CH:11]=[C:10]([Cl:14])[CH:9]=[C:8]([Cl:15])[C:7]=1[N:6]1[C:2]2=[N:1][C:31]([CH2:30][C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=3)=[N:21][C:19](=[O:20])[C:3]2=[C:4]([CH:16]([CH3:18])[CH3:17])[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27332463-Methoxyphenylacetyl chlorideHCID 185406305-Amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

Product 1

HCID 178490012HCID 178490012, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Part C: To a stirred solution of 167 mg (0.5 mmol) of 5-amino-3-isopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 6 mL of absolute ethanol was added 550 mg (3.0 mmol) of 3-methoxyphenylacetyl chloride followed by 2.3 mL (6.0 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 5 mL of 10% aq. HOAc, cooled to ambient temperature, and filtered. The filtrate was washed with 6 mL of 1:1 water-methanol then 6 mL of 1:1 ether-hexanes. The off-white solid was briefly air-dried to give 170 mg (76%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(3-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one, mp 204-205° C., Mass Spec: 477(M+H)+.

Workup

  1. temperatureat reflux
  2. customthe heating mantle was then removed
  3. additionThe reaction was treated with 5 mL of 10% aq. HOAc
  4. filtrationfiltered
  5. washThe filtrate was washed with 6 mL of 1:1 water-methanol
  6. customThe off-white solid was briefly air-dried

Sources & evidence

ORD record
ord-bbe632a3fb3d40588d438c9648eea4d5
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

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