Pentamethyldiethylenetriamine → (4-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

Participants

Role	Name	HCID	Charge
Reactant	Pentamethyldiethylenetriamine	HCID 18196	—
Reactant	1-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehyde	HCID 13224143	—
Reactant	Tert-butyl(2-ethyl-5-fluorophenoxy)dimethylsilane	HCID 57803899	—
Reactant	Butyllithium	HCID 178418339	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	(4-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol	HCID 57803708	67.5%

Reaction Conditions

Temperature	-40 °C

Reaction Steps

BuLi (0.67 mL, 1.6 M in hexanes, 1.1 mmol) was added dropwise to a solution of Intermediate 386.3 (250 mg, 0.98 mmol) and PMDTA (0.20 mL, 0.98 mmol) in THF (4 mL) at −78° C. The mixture was warmed to −40° C. and stirred for 30 min. After recooling the reaction to −78° C., Intermediate 386.1 (203 mg, 1.08 mmol) in THF (2 mL) was added and the mixture was warmed to ambient temperature over 2 h. Water was added to the mixture and it was extracted with EtOAc. The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (hexanes, EtOAc) yielded 292 mg of Intermediate 386.4 as a clear oil. LCMS 442.34 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07576098B2
Source dataset	uspto-grants-2009_08
ORD ID	ord-5e6655e0ae8245958850c9e5e6945c7e
Source note	uspto-grants-2009_08