Diisopropylethylamine → 3-(4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylamino)-5-nitropyrimidin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-(6-Cyano-1H-benzimidazol-1-yl)-5-nitropyrimidin-4-yl thiocyanate	HCID 53389590	—
Reactant	(1R,4R)-4-(tert-Butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine	HCID 59704938	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	3-(4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-ylamino)-5-nitropyrimidin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile	HCID 66970817	78.6%

Reaction Steps

A solution of (1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-amine (4.0 g) and DIEA (5.3 mL) in anhydrous THF (20 mL) were added via syringe over 1 min to 6-cyano-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazole (3.43 g, 10.601 mM) in THF at 0° C. The resulting solution was allowed to warm slowly to RT overnight, then partitioned between water and DCM. Column purification (1% MeOH/DCM) gave the titled product (5.21 g), MH+=666.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07884109B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-0d8df0aaba404e1dbf5f6432d454fc77
Source note	uspto-grants-2011_02