Tetrabutylammonium Fluoride → [3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-yl]-methanol

Participants

Role	Name	HCID	Charge
Reactant	Tetrabutylammonium Fluoride	HCID 2724141	—
Reactant	(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amine	HCID 57936167	—
Reactant	2-[[6-(2-Tert-butylsilyloxypropan-2-yl)indol-1-yl]methoxy]ethyl-trimethylsilane	HCID 131727752	—
Product	[3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-yl]-methanol	HCID 57936184	—

Reaction Steps

[3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-yl]-methanol was prepared as described in Example 215, starting from 6-(tert-butyl-dimethyl-silanyloxymethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole and (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine, followed by selective cleavage of the TBDMS-protecting group with TBAF. Yield: 7.1 g (93%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07615562B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-2e26fbab360140fbb2ddb0a45631e824
Source note	uspto-grants-2009_11