Diisopropylethylamine → 4-(2,4-Dimethoxybenzylamino)-3-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Aminotetrahydropyran	HCID 419223	—
Reactant	2-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate	HCID 56605211	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4-(2,4-Dimethoxybenzylamino)-3-(5-nitro-4-(tetrahydro-2H-pyran-4-ylamino)pyrimidin-2-ylamino)benzonitrile	HCID 59705005	98.9%

Reaction Steps

To the suspension of 0.92 g (2.0 mmol) of 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile in 40 mL anhydrous THF was added 0.22 g (2.2 mmol) 4-amino-tetrahydropyran, then 0.7 mL (4.0 mmol) N,N-diisopropylethylamine. The mixture was stirred at room temperature under Argon balloon for 16 hrs till HPLC showed the completion of reaction. The mixture became clear then. The orange-red solution was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 1.0 g orange-yellow 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-5a2859aca78349d58b30ecb3ff309dcb
Source note	uspto-grants-2011_03