Tetrabutylammonium Fluoride → HCID 58300158, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrabutylammonium Fluoride	HCID 2724141	—
Reactant	N-(5-(4-(2-((tert-butyl(dimethyl)silyl)oxy)ethyl)-1-piperidinyl)-2-pyridinyl)-9-cyclopentyl-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine	HCID 58300008	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 58300158	HCID 58300158	70%

Reaction Steps

Compound 294 (78 mg, 132 mop was dissolved in dry THF (3 mL). Tetrabutylammonium fluoride, 1.0M in THF (1.00 mL, 1.00 mmol) was added and the reaction stirred at room temperature for 4 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA) afforded compound 291 as a beige solid (44 mg, 70%). 1H NMR (500 MHz, DMSO-d6) δ 11.60-11.85 (m, 2 H) 9.49 (s, 2 H) 8.19-8.24 (m, 2 H) 8.13-8.19 (m, 2 H) 8.05-8.10 (m, 2 H) 7.96-8.04 (m, 2 H) 7.61-7.71 (m, 2 H) 5.48 (s, 1 H) 3.64 (d, J=11.98 Hz, 2 H) 3.44 (t, J=6.48 Hz, 2 H) 2.71-2.90 (m, 2 H) 2.20 (br. s., 2 H) 2.09 (br. s., 2 H) 2.00 (br. s., 2 H) 1.66-1.82 (m, 4 H) 1.52-1.66 (m, 1 H) 1.37 (d, J=6.60 Hz, 2 H) 1.28 (none, 2 H) ppm.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08841312B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-49ce65021af14ab78231a52ce558e5c3
Source note	uspto-grants-2014_09