Benzylamine → N-benzyl-4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Benzylamine	HCID 7504	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic Acid	HCID 71235039	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-benzyl-4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxamide	HCID 71235045	22%

Reaction Steps

4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxylic acid (2.2 g, 6.47 mmol), benzylamine (1.0 g, 9.34 mmol) and HATU (2.95 g, 7.76 mmol) were dissolved in 60 mL of THF, DIEA (N,N-diiso-propylethylamine, 3.36 mL, 19.41 mmol) was added dropwise, reacted at room temperature for 8 h. To the reaction solution was added 100 mL of water and then extracted with dichloromethane (50 mL×3), dried with anhydrous sodium sulfate, dried by rotation, the solid was separated with silica gel column (dichloromethane:methanol=100:1) to obtain a white solid N-benzyl-4-(3-chloro-4-methoxybenzyloxy)-2-(methylmercapto)pyrimidine-5-carboxamide 600 mg, 22% yield.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08980904B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-78133963d020484991ba3f03da85d106
Source note	uspto-grants-2015_03