Methylamine → HCID 19898806, compound

HRID 1196501Notes

Reaction equation

HRID 1196501 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)C=CN=[CH:2]1.CN>O1CCCC1.O>[CH3:2][NH:1][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 6329MethylamineHCID 19898814HCID 19898814, compound

Product 1

HCID 19898806HCID 19898806, compoundYield 39.2%

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 monomethylamine in 10 ml of dry tetrahydrofuran added dropwise from a needle and syringe. After stirring for 36 hours the reaction mixture was diluted with 100 ml of water and the resulting solid collected by filtration (1.7 g). The crude product was recrystallized from acetonitrile to yield 1.1 g (38.9%) of beige crystals, mp 207°-208° C.

Workup

  1. additionadded dropwise from a needle and syringe
  2. filtrationthe resulting solid collected by filtration (1.7 g)
  3. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-f4f6765ab23546669a51e9a73f26ee5a
Source dataset
uspto-grants-1992_05
Patent number
US05114944

Reaction notes

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