Sodium ethoxide → HCID 178489874, compound

HRID 411572Notes

Reaction equation

HRID 411572 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]2[CH2:18][CH2:17]2)[C:3]=1[C:19]([NH2:21])=[O:20].[OH:22][C:23]1[CH:24]=[C:25]([CH2:31][C:32](OCC)=O)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].[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:32]([CH2:31][C:25]3[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([OH:22])[CH:24]=3)=[N:21][C:19](=[O:20])[C:3]2=[C:4]([CH:16]2[CH2:17][CH2:18]2)[NH:5]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5324706Ethyl 2-(3-hydroxy-4-methoxyphenyl)acetateHCID 185407045-Amino-3-cyclopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide

Product 1

HCID 178489874HCID 178489874, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 146 mg (0.42 mmol) of 5-amino-3-cyclopropyl-1-(2,4,6-trichlorophenyl)pyrazole-4-carboxamide in 6 mL of absolute ethanol was added 533 mg (2.53 mmol) of ethyl 3-hydroxy-4-methoxyphenylacetate followed by 1.91 mL (5.1 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 46 mg (22%) of 1-(2,4,6-trichlorophenyl)-3-cyclopropyl-6-(3-hydroxy-4-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one. Mass Spec.: 489 (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-2be9bc8665cd4dc2baa0678d8facd639
Source dataset
uspto-grants-2003_05
Patent number
US06559152B2

Reaction notes

Loading…