Sodium hydride → 4-Bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-5-amine

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To a solution of 4-bromo-1H-pyrazol-5-amine (1 g, 6.17 mmol) in THF (20 mL) at 0° C. was added NaH (0.494 g, 12.35 mmol) and stirred at the same temperature for 30 mins To this mixture was then added SEM-Cl (1.095 mL, 6.17 mmol) and slowly allowed to raise to rt and stirred at rt for 1 h. The reaction mix was then quenched with Satd. NH4Cl and then extracted with EtOAc, dried over Na2SO4, filtered, and concentrated. Purification by normal phase chromatography afforded 221A (1.45 g, 80% yield) as a pale yellow oil. MS (ESI) m/z: 292.0 (M+H)+.

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