Dimethyl Sulfoxide → 4-(2-(4-aminophenylthio)pyridin-3-yl)-N-methylpyrimidin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Dimethyl Sulfoxide	HCID 679	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	4-Aminothiophenol	HCID 14510	—
Reactant	4-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamine	HCID 16109004	—
Solvent	Water	HCID 962	—
Product	4-(2-(4-aminophenylthio)pyridin-3-yl)-N-methylpyrimidin-2-amine	HCID 57756243	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

To 4-aminothiophenol (1.70 g, 13.6 mmol) and Cs2CO3 (8.90 g, 27.2 mmol) was added DMSO (18 mL). The mixture was stirred for 5 minutes at 100° C. before 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (3.00 g, 13.6 mmol) was added. The resulting mixture was stirred for 16 hours at 130° C., then diluted with water and the resulting solid filtered. After washing the solid with water and Et2O it was dried under vacuum to yield the desired product as a tan solid. MS m/z=310 [M+1]+. Calc'd for C16H15N3S: 309.40.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08022221B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-5d8052b4f98840cdb4794e2f2844a18b
Source note	uspto-grants-2011_09