Dimethylamine → HCID 19898797, compound

HRID 1196503Notes

Reaction equation

HRID 1196503 reaction equation
[N:1]1([C:6](=[O:24])[CH2:7][C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[N:13][C:12]=23)[CH:5]=CN=[CH:2]1.CNC>O1CCCC1.O>[CH3:5][N:1]([CH3:2])[C:6](=[O:24])[CH2:7][C:8]1[C:9]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)=[N:10][N:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=12

Participants

5

Reactant 2

HCID 674DimethylamineHCID 19898814HCID 19898814, compound

Product 1

HCID 19898797HCID 19898797, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred slurry of 3.2 g (0.010 mole) of 3-[2-(1H-imidazole-1-yl)-2-oxoethyl]-2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine (prepared from 2-(4-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-acetic acid and 1,1'-carbonyldiimidazole) in 20 ml of dry tetrahydrofuran was treated with 3 ml of dimethylamine in 10 ml of dry tetrahydrofuran. After stirring for 16 hours, the reaction mixture was diluted with 100 ml of water and the precipitated solid collected by filtration (1.4 g). The crude product was purified by a liquid-solid extraction in a soxhlet using isopropyl ether as the extracting solvent. Filtration yielded 1.6 g (33.6%) of golden yellow crystals, mp 163.5°-165° C.

Workup

  1. filtrationthe precipitated solid collected by filtration (1.4 g)
  2. customThe crude product was purified by a liquid-solid extraction in a soxhlet
  3. filtrationFiltration

Sources & evidence

ORD record
ord-7a2ff09d17ec4899b644c5c7e2dfb53a
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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