Hydrochloric Acid → 4,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Tert-butyl 5-(2-hydroxypropan-2-yl)-4-(2-(tetrahydro-2h-pyran-2-yloxy)ethyl)thiazol-2-ylcarbamate	HCID 87179654	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	4,4-dimethyl-4H,6H,7H-pyrano[4,3-d][1,3]thiazol-2-amine	HCID 87179372	51.3%

Reaction Steps

To a solution of Example 89D (4.6 g, 11 mmol) in THF (90 mL) was added conc. HCl (6.9 mL). The reaction mixture was refluxed for overnight and then cooled. The mixture was basified with 5N NaOH ((17 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-10% methanol in dichloromethane) to afford 1.04 g (51%) of the title compound. MS (ESI+) m/z 185 (M+H)+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08865753B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-3fe21f5bdde649dca86a714f8f3e263f
Source note	uspto-grants-2014_10