Phosphorus oxychloride → Ethyl 2-(7-chloro-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 584783Notes

Reaction equation

HRID 584783 reaction equation
P(Cl)(Cl)([Cl:3])=O.[C:6]1([CH3:32])[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:7]=1[C:14]1[C:15]([CH3:31])=[N:16][N:17]2[C:22](=O)[C:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:20]([CH3:30])[NH:19][C:18]=12.C(=O)(O)[O-].[Na+]>>[Cl:3][C:22]1[N:17]2[N:16]=[C:15]([CH3:31])[C:14]([C:7]3[C:8]([CH3:13])=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=3[CH3:32])=[C:18]2[N:19]=[C:20]([CH3:30])[C:21]=1[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178470721HCID 178470721, compound

Product 1

HCID 22249832Ethyl 2-(7-chloro-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 103.2%

Procedure

Phosphorus oxychloride (1.7 g) was added to ethyl 2-(3-mesityl-2,5-dimethyl-7-oxo-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-yl)acetate (120 mg) of Reference Example 27 at room temperature, followed by stirring for one hour under heating under reflux. After cooling, the reaction solution was poured onto ice. The reaction mixture was basified with an aqueous saturated solution of sodium bicarbonate, and then extracted twice with ethylacetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give the title compound (130 mg) as a reddish brown oil.

Workup

  1. temperatureunder heating
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. additionthe reaction solution was poured onto ice
  5. extractionextracted twice with ethylacetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-aed056b633f642de9bf31dd5c448eec2
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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