Methyl iodide → 5-(4-Chlorophenyl)-2-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine

Iodomethane (0.65 ml) was added to a solution of 5-(4-chlorophenyl)-2-pyridin-4-ylpyrimidine (0.311 g) in a mixture of chloroform (18 ml) and methanol (2 ml), and the reaction stirred at room temperature, in a stoppered flask, for 13 days. The solvents were then removed under reduced pressure, and the residue was re-suspended in a mixture of methanol (10 ml) and water (2 ml), cooled in an ice-bath and treated portionwise with sodium borohydride (0.088 g) (CAUTION-vigorous effervescence). The reaction was stirred in the ice-bath for 1.5 h, at room temperature for a further 1.5 h, then treated with saturated ammonium chloride (30 ml) followed by water (20 ml), and the resultant suspension was extracted with ethyl acetate (50 ml, then 2×25 ml). The combined organic extracts were washed with water (3×25 ml), saturated brine (20 ml), dried (Na2SO4) and evaporated under reduced pressure to furnish the title compound as a cream solid (0.310 g, 94%).

1. customThe solvents were then removed under reduced pressure
2. additionthe residue was re-suspended in a mixture of methanol (10 ml) and water (2 ml)
3. temperaturecooled in an ice-bath
4. additiontreated portionwise with sodium borohydride (0.088 g) (CAUTION-vigorous effervescence)
5. stirringThe reaction was stirred in the ice-bath for 1.5 h, at room temperature for a further 1.5 h
6. additiontreated with saturated ammonium chloride (30 ml)
7. extractionthe resultant suspension was extracted with ethyl acetate (50 ml
8. washThe combined organic extracts were washed with water (3×25 ml), saturated brine (20 ml)
9. dry with materialdried (Na2SO4)
10. customevaporated under reduced pressure

ORD record

ord-01a10203dae74ceba984ec05696d92b7

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06809100B2