Hydrochloric Acid → 3-[(Ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-amine

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To a 25 mL round bottom was added 4-(ethyloxy)-3-oxobutanenitrile (550 mg, 4.33 mmol), isopropyl hydrazine hydrochloride (478 mg, 4.33 mmol), and HCl (2.163 mL, 4.33 mmol) in Ethanol (10 mL). The reaction mixture was stirred at the room temperature overnight. The reaction mixture was then evaporated, and partitioned between 20 mL of ethyl acetate and 20 mL of 1 M Na2CO3. The organic layer was washed with brine, filtered and evaporated. 3-[(Ethyloxy)methyl]-1-(1-methylethyl)-1H-pyrazol-5-amine (520 mg, 2.84 mmol, 65.6% yield) was isolated as yellow oil. The product was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) ppm 1.09 (t, J=7.07 Hz, 3 H) 1.26 (d, J=6.57 Hz, 6 H) 3.40 (q, J=6.91 Hz, 2 H) 4.16 (s, 2 H) 4.32 (quin, J=6.57 Hz, 1 H) 5.06 (s, 2 H) 5.22 (s, 1 H)

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