p-Toluenesulfonic acid → 6-Bromo-2-methylpyrazolo[1,5-a]pyrimidine

HRID 1926726Notes

Reaction equation

HRID 1926726 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[NH:4][N:3]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[Br:19][CH:20]([CH:23]=O)[CH:21]=O>CCO>[Br:19][C:20]1[CH:21]=[N:7][C:5]2[N:4]([N:3]=[C:2]([CH3:1])[CH:6]=2)[CH:23]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 749452-BromopropanedialHCID 178418690HCID 178418690, compound

Product 1

HCID 159800416-Bromo-2-methylpyrazolo[1,5-a]pyrimidineYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-methyl-1H-pyrazol-5-amine a12 (64.8 mmol, 1 eq, 6.3 g) in EtOH (100 ml), in the presence of PTSA, is added bromomalonaldehyde x9 (64.8 mmol, 1 eq, 9.79 g). The mixture is heated at 80° C. for 12 hours. The solvent is evaporated under reduce pressure and the residue purified by chromatography on silicagel (hexane/AcOEt: 93/7 (v/v)). 6-bromo-2-methylpyrazolo[1,5-a]pyrimidine x14 is obtained as a white solid (4.04 g).

Workup

  1. customThe solvent is evaporated
  2. customthe residue purified by chromatography on silicagel (hexane/AcOEt: 93/7 (v/v))

Sources & evidence

ORD record
ord-a2ff1b05b0994f04a067cfe74db3ff2d
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

Loading…