Acetic Acid → 3-Tert-butyl-1-((tetrahydro-2h-pyran-2-yl)methyl)-1h-pyrazol-5-amine

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Hydrazine	HCID 9321	—
Reactant	N'-[3-tert-butyl-1-(oxan-2-ylmethyl)pyrazol-5-yl]-N,N-dimethylmethanimidamide	HCID 87440113	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3-Tert-butyl-1-((tetrahydro-2h-pyran-2-yl)methyl)-1h-pyrazol-5-amine	HCID 67544533	—

Reaction Conditions

Temperature	85 °C

Reaction Steps

To a solution of Example 63B (0.9 g, 3.1 mmol) in dioxane (10 mL) were added hydrazine (0.12 mL, 3.7 mmol, Aldrich) and acetic acid (0.35 mL, 6.2 mmol). After stirring at 85° C. for 16 h, the reaction mixture was cooled and quenched with saturated NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide the title compound. MS (APCI+) m/z 238 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09193713B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-eb0c5c8d653543a98410b3cd27d7cab4
Source note	uspto-grants-2015_11