Triphenylphosphine → 3-tert-butyl-1-(3-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)phenyl)-1H-pyrazol-5-amine

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DIAD (847 μL, 4.32 mmol) was added slowly to a solution of 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenol (for reference procedure see US 2006/35922, which is incorporated herein by reference in its entirety; 500 mg, 2.16 mmol), 2-(tetrahydro-pyran-2-yloxy)-ethanol (439 μL, 3.25 mmol), and triphenylphosphine (1.13 g, 4.32 mmol) in THF (10.0 mL) and stirred for 72 h. The reaction mixture was partitioned between EtOAc (75 mL) and H2O (75 mL), and the aqueous layer extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered and evaporated in vacuo. Purification by FCC, using 5-60% EtOAc in cyclohexane, gave semi-pure title compound (1.26 g). This was used in the next reaction without further purification. LCMS (Method 4): Rt 2.77, m/z 360 [MH+].

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