Chloroform → Ethyl 5,7-dichloropyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 869712Notes

Reaction equation

HRID 869712 reaction equation
O[C:2]1[CH:7]=C(O)[N:5]2[N:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+].[CH:27]([Cl:30])(Cl)Cl>>[Cl:19][C:2]1[CH:7]=[C:27]([Cl:30])[N:5]2[N:9]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:11]=[C:4]2[N:3]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178468554HCID 178468554, compound

Product 1

HCID 86674517Ethyl 5,7-dichloropyrazolo[1,5-a]pyrimidine-2-carboxylate

Procedure

A suspension of ethyl 5,7-dihydroxypyrazolo[1,5-a]pyrimidine-2-carboxylate (9.59 g, 43.0 mmol) and phosphorous oxychloride (20.0 mL, 215 mmol) was refluxed for 1 hr. After being cooled to ambient temperature, the reaction mixture was poured into saturated sodium bicarbonate and chloroform. The organic layer was separated and aqueous layer was extracted with chloroform. The organic layer was combined and concentrated in vacuo to give ethyl 5,7-dichloropyrazolo[1,5-a]pyrimidine-2-carboxylate. MS (APCI): m/z 260/262 (M+H).

Workup

  1. temperaturewas refluxed for 1 hr
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with chloroform
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c44cbd0f641f4843b26a7f600cad244f
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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