HCID 86711218, compound → HCID 68276104, compound

HRID 1475944Notes

Reaction equation

HRID 1475944 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:3]=1.[H][H]>C(Cl)Cl.CO.C(N(CC)CC)C.[Pd]>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]2[CH:10]=[C:6]3[N:5]=[C:4]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:3]=[CH:2][N:7]3[N:8]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 2

HCID 86711218HCID 86711218, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68276104HCID 68276104, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylate (767 mg; 2.31 mmol) in methylene chloride (10 mL), methanol (10 mL) and triethylamine (2 mL) was added 10% Pd on carbon (77 mg) and the mixture was cooled to 0° C. The reaction flask was put under vacuum and then hydrogen was introduced using a balloon. A second cycle of vacuum and hydrogen purge was performed and the mixture was stirred at 0° C. for 1.5 h. The mixture was flushed with two cycles of vacuum and nitrogen, diluted with methylene chloride and then filtered through a 0.45 micron filter to remove the catalyst. Concentration afforded the crude product which was triturated in methanol (25 mL) and filtered to afford 485 mg (71%) of the title compound. LCMS m/z 298.1 (M+H)+, ret. time=2.53 min.

Workup

  1. customA second cycle of vacuum and hydrogen purge
  2. customThe mixture was flushed with two cycles of vacuum and nitrogen
  3. additiondiluted with methylene chloride
  4. filtrationfiltered through a 0.45 micron
  5. filtrationfilter
  6. customto remove the catalyst
  7. concentrationConcentration
  8. customafforded the crude product which
  9. customwas triturated in methanol (25 mL)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-bf4b4ece76c24398b4abbdce9fdf7b66
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

Loading…