Sodium Hydroxide → HCID 67123869, compound

HRID 1500756Notes

Reaction equation

HRID 1500756 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:4]2=[C:3]([C:10]([NH2:12])=O)[CH:2]=1.C(=O)([O-])O.[Na+].[OH-].[Na+]>P(Cl)(Cl)(Cl)=O>[N:1]1[N:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:4]2=[C:3]([C:10]#[N:12])[CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 67123597HCID 67123597, compound

Product 1

HCID 67123869HCID 67123869, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of crude pyrazolo[1,5-a]pyrazine-3-carboxamide (Preparation 24a, 6.66 g) in phosphoryl trichloride (80 mL) was heated to reflux for 2.5 hours. The reaction mixture was then poured onto a saturated aqueous sodium hydrogen carbonate solution (200 mL) and then the pH was adjusted to 7-8 by addition of a 10% aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate, the organic layer was dried (MgSO4) and evaporated and the resulting residue was purified by flash chromatography (1:1 hexanes/ethyl acetate) to give the title compound (3.10 g, 52%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe resulting residue was purified by flash chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-08a5524d3a0a415d92722ac8ed9bae60
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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