Acetic Acid → HCID 13133064, compound

HRID 1285492Notes

Reaction equation

HRID 1285492 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:4](C=O)=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][C:7]#[N:8].[CH3:16][C:17]1[NH:21][N:20]=[C:19]([NH2:22])[CH:18]=1.[OH-].[Na+].[C:25](O)(=O)C>O>[NH2:8][C:7]1[N:20]2[N:21]=[C:17]([CH3:16])[CH:18]=[C:19]2[N:22]=[CH:25][C:6]=1[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 20249155HCID 20249155, compound

Product 1

HCID 13133064HCID 13133064, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

21.3 g of m-trifluoromethyl-2-formylbenzyl cyanide and 9.7 g of 3(5)-amino-5(3)-methylpyrazole in 100 ml of glacial acetic acid were refluxed for 4 hours. The mixture was cooled and was then diluted with 500 ml of water, the pH was brought to 5-6 with 2N NaOH solution, and the oily product which precipitated crystallized after trituration. The crystals were filtered off under suction and then washed several times with water and dried under reduced pressure at 50° C. 25.0 g of 7-amino-2-methyl-6-(3'-trifluoromethylphenyl)-pyrazolo[1,5-a]pyrimidine of melting point 176° C. were obtained (Compound 10).

Workup

  1. temperatureThe mixture was cooled
  2. customthe oily product which precipitated
  3. customcrystallized after trituration
  4. filtrationThe crystals were filtered off under suction
  5. washwashed several times with water
  6. customdried under reduced pressure at 50° C

Sources & evidence

ORD record
ord-8b8f7edd31144a37bd72a185311ecd81
Source dataset
uspto-grants-1986_01
Patent number
US04567263

Reaction notes

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