Ethanol → 5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazide

Reaktionsgleichung

[CH3:1][Si:2]([CH3:26])([CH3:25])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[N:17]3[CH:18]=[CH:19][N:20]=[C:16]3[CH:15]=[C:14]([C:21]([O:23]C)=O)[N:13]=2)[CH:9]=[N:8]1.CCO.O.[NH2:31][NH2:32]>>[CH3:26][Si:2]([CH3:1])([CH3:25])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2[N:17]3[CH:18]=[CH:19][N:20]=[C:16]3[CH:15]=[C:14]([C:21]([NH:31][NH2:32])=[O:23])[N:13]=2)[CH:9]=[N:8]1

Komponenten

Edukt 3

HCID 702Ethanol

HCID 24654Hydrazine hydrate (1:1)

HCID 67456583methyl 5-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate

Produkt 1

HCID 674592615-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazideAusbeute 92,7 %

Versuchsvorschrift

In a 20 mL flask, methyl 5-(1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylate (Example 122; Step C) (50 mg, 0.13 mmol) was dissolved in EtOH (540 μL, 0.13 mmol). To this was added a large excess of hydrazine hydrate (104 μL, 3.3 mmol). The reaction mixture was refluxed for 1 hour, and then concentrated down to dryness. The residue was diluted in EtOAc and washed with water and brine. The organic layer was dried with MgSO4, filtered and concentrated in vacuo to afford 5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carbohydrazide (45 mg, 90% yield) as a yellow oil. MS (apci) m/z=374.4 (M+H).