6-Chloronicotinic acid → N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-6-chloro-nicotinamide

Participants

Role	Name	HCID	Charge
Reactant	6-Chloronicotinic acid	HCID 79222	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	5,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dione	HCID 10954202	—
Solvent	Methanol	HCID 887	—
Product	N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-6-chloro-nicotinamide	HCID 86664815	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A mixture of 5,6-diamino-3-propyl-1H-pyrimidine-2,4-dione (2.0 g, 11.0 mmol), 6-Chloro nicotinic acid (1.86 g, 11.8 mmol) in methanol (40 ml) were cooled to 0° C. and added EDCI.HCl (4.2 g, 22 mmol). The reaction mixture was stirred at 25° C. for 20 hours and the solvents were removed under reduced pressure. To this residue water (20 ml) was added and the precipitate was filtered off, and washed sequentially with cold water (20 ml) and methanol (5 ml) to obtain N-(6-Amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-6-chloro-nicotinamide as an off white solid. (2.47 g, 70%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08859566B2
Source dataset	uspto-grants-2014_10
ORD ID	ord-3f6513c3056b420dbdd1658250142df8
Source note	uspto-grants-2014_10