Ammonia → HCID 86630688, compound

HRID 503787Notes

Reaction equation

HRID 503787 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 is dissolved in 80 ml dichloromethane. 80 ml brine, 40 ml ammonia solution 25% w/w and 2.47 g zinc powder are added and the mixture is stirred at room temperature for 2 d. Four additional portions of 4.2 equivalents zinc powder are added over 4 days. The reaction mixture is filtrated over kieselgur and washed with dichloromethane and water. The organic phase is separated and the water phase extracted with dichloromethane. The combined dichloromethane phase is dried over Na2SO4 and the solvent is evaporated. The residue is purified on silica gel (dichloromethane/ethyl acetate) to yield the desired product.

Workup

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

Sources & evidence

ORD record
ord-3418e1461b2d4ecba87b2ac3d06038ad
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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