Ammonia → HCID 86630688, compound

HRID 1851212Notes

Reaction equation

HRID 1851212 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]([CH3:18])[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:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:15]=[C:16]([CH3:18])[CH:17]=[C:4]2[N:3]=1

Participants

6

Reactant 2

HCID 222AmmoniaHCID 82274691HCID 82274691, compound

Product 1

HCID 86630688HCID 86630688, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2.47 g 5,7-dichloro-2-methyl-6-phenylpyrazolo[1,5-a]pyrimidine was dissolved in 80 mL dichloromethane. 80 mL brine, 40 mL ammonia solution 25% w/w and 2.47 g zinc powder were added and the mixture was stirred at room temperature for 2 d. Four additional portions of 4.2 equivalents zinc powder were added over 4 days. The reaction mixture was filtered through Celite and washed with dichloromethane and water. The organic phase was separated and the water phase extracted with dichloromethane. The combined dichloromethane phase was dried over Na2SO4 and the solvent was evaporated. The residue was purified on silica gel (dichloromethane/ethyl acetate) to yield the desired product.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with dichloromethane and water
  3. customThe organic phase was separated
  4. extractionthe water phase extracted with dichloromethane
  5. dry with materialThe combined dichloromethane phase was dried over Na2SO4
  6. customthe solvent was evaporated
  7. customThe residue was purified on silica gel (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-ecf4d8cf654144019722e630319caceb
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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