Diisopropylethylamine → (R)-4-(2,4-Dimethoxybenzylamino)-3-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(R)-8-fluorochroman-4-amine	HCID 46911919	—
Reactant	2-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate	HCID 56605211	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(R)-4-(2,4-Dimethoxybenzylamino)-3-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrile	HCID 59704995	96.2%

Reaction Steps

(R)-8-Fluorochroman-4-amine (HCl salt, 0.45 g, 2.2 mmol) was dissolved in 1 mL DMSO with 1.7 mL N,N-diisopropylethyl amine (9.7 mmol) in 40 mL anhydrous THF. To this solution was added 0.93 g (2.0 mmol) 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile. The slightly cloudy mixture was stirred at room temperature for 16 hrs under Argon balloon till HPLC showed the completion of reaction. The mixture became clear then. The reaction mixture was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 1.1 g dark red solid as the crude product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915268B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-7ca6aab196f74a56b6331b66d36c3393
Source note	uspto-grants-2011_03