HCID 57743058, compound → HCID 57743030, compound

HRID 1926794Notes

Reaction equation

HRID 1926794 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[F:18]>CC(O)=O.[Zn]>[F:18][C:3]1[C:4]([CH3:17])=[N:5][C:6]2[N:7]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=2)[CH:2]=1

Participants

4

Reactant 1

HCID 57743058HCID 57743058, compound

Product 1

HCID 57743030HCID 57743030, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-chloro-6-fluoro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine x136 (22.9 mmol, 1 eq, 6 g) in 150 ml of AcOH at 0° C., is added zinc dust (68 mmol, 3 eq, 4.5 g). The mixture is stirred at 25° C. overnight. After evaporation of the solvent under reduced pressure, the crude product is poured on ice and quenched with a saturated aqueous NaHCO3 solution and extracted with AcOEt. The cumulated organic layers are washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure to yield 6-fluoro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine x139.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. additionthe crude product is poured on ice
  3. customquenched with a saturated aqueous NaHCO3 solution
  4. extractionextracted with AcOEt
  5. washThe cumulated organic layers are washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-68acb8b0019046cbbf2961b7a0a36d24
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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