Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane → 4-(3-(1-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)-2-hydroxypropoxy)phenol

Participants

Role	Name	HCID	Charge
Reactant	Tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane	HCID 19385012	—
Reactant	1-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine	HCID 69040995	—
Solvent	iPrOH DMSO	HCID 87082799	—
Product	4-(3-(1-(5-(4-Fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-ylamino)-2-hydroxypropoxy)phenol	HCID 24936491	45%

Reaction Steps

Synthesis followed SP6 (iPrOH:DMSO 1:1, 10 h), using 200 μmol tert-butyldimethyl(4-(oxiran-2-ylmethoxy)phenoxy)silane and 1-(5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl)piperidin-4-amine to give O-silylated intermediate upon purification by prep. HPLC (reversed phase) with 45% yield. Product was obtained by deprotection according to SP7 and purification by prep. HPLC (reversed phase) with 74% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08207174B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-928f906070374f1fb48b21888822a012
Source note	uspto-grants-2012_06