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

HRID 965990Notes

Reaction equation

HRID 965990 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-657281b4b620438c84f2b8977eba7b50
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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