Ammonia → HCID 86630699, compound

HRID 1915614Notes

Reaction equation

HRID 1915614 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=[C:4]2[N:3]=1.N>ClCCl.[Cl-].[Na+].O.[Zn]>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][N:5]2[N:15]=[C:16]([C:18]([O:20][CH3:21])=[O:19])[CH:17]=[C:4]2[N:3]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 86630700HCID 86630700, compound

Product 1

HCID 86630699HCID 86630699, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

2.00 g methyl 5,7-dichloro-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate are dissolved in 40 ml dichloromethane. 40 ml brine, 20 ml ammonia solution 25% w/w and 1.22 g zinc powder are added and the mixture is stirred at 60° C. for 3 h. The reaction mixture is filtrated over kieselgur and is washed with dichloromethane and water. The organic phase is separated and the water phase is extracted with dichloromethane. The combined dichloromethane phase is dried over Na2SO4 and evaporated. The crude product contains methyl 5,7-dichloro-6-phenylpyrazolo[1,5-a]pyrimidine-2-carboxylate. The crude product is dissolved again in 20 ml dichloromethane. 20 ml brine, 10 ml ammonia solution 25% w/w and 0.60 g zinc powder are added and the mixture is stirred at 60° C. for 45 min. The reaction mixture is filtrated over kieselgur and washed with dichloromethane and water. The organic phase is separated and the water phase is extracted with dichloromethane. The combined dichloromethane phase is dried over Na2SO4, the solvent is evaporated and the residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the desired compound.

Workup

  1. filtrationThe reaction mixture is filtrated over kieselgur
  2. washis washed with dichloromethane and water
  3. customThe organic phase is separated
  4. extractionthe water phase is extracted with dichloromethane
  5. dry with materialThe combined dichloromethane phase is dried over Na2SO4
  6. customevaporated
  7. dissolutionThe crude product is dissolved again in 20 ml dichloromethane
  8. addition20 ml brine, 10 ml ammonia solution 25% w/w and 0.60 g zinc powder are added
  9. stirringthe mixture is stirred at 60° C. for 45 min
  10. filtrationThe reaction mixture is filtrated over kieselgur
  11. washwashed with dichloromethane and water
  12. customThe organic phase is separated
  13. extractionthe water phase is extracted with dichloromethane
  14. dry with materialThe combined dichloromethane phase is dried over Na2SO4
  15. customthe solvent is evaporated
  16. customthe residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-0c72703be5304b0dba6529e275f06859
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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