Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-methylpyridin-2-yl)phenyl)guanidine

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Chloro-1-methylpyridinium iodide	HCID 167069	—
Reactant	N,N'-Di-Boc-thiourea	HCID 5193990	—
Reactant	2-(3-Aminophenyl)-4-methylpyridine	HCID 18667616	—
Solvent	Dichloromethane	HCID 6344	—
Product	N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-methylpyridin-2-yl)phenyl)guanidine	HCID 135710945	62.1%

Reaction Steps

To a suspension of 3-(4-methylpyridin-2-yl)aniline (276 mg), N,N′-bis (tert-butoxycarbonyl )thiourea (539 mg) and diisopropylethyl-amine (0.601 ml) in dichloromethane (15 ml) was added 1-methyl-2-chloropyridinium iodide (498 mg), and the mixture was stirred for 2.5 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 45 g, n-hexane:ethyl acetate=9:1) to give N,N′-bis(tert-butoxycarbonyl) -N″-(3-(4-methylpyridin-2-yl)phenyl)guanidine (397 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06521643B1
Source dataset	uspto-grants-2003_02
ORD ID	ord-02bb010c8e694a0fa4962319badc36b0
Source note	uspto-grants-2003_02