Ethyl Acetate → 6-chloro-4-N-prop-2-enylpyrimidine-4,5-diamine

A solution of 8 g 5-amino-4,6-dichloropyrimidine, 5 ml propargylamine and 42 ml diisopropyl ethyl amine in 100 ml butanol was stirred for 6 hours and 10 minutes in a nitrogen atmosphere at 140° C. Ethyl acetate and H2O were added to the reaction mixture, and this mixture was filtered through Celite, and the residue was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the residue was purified by silica gel column chromatography (eluted with ethyl acetate:n-hexane=1:1), and the objective fractions were concentrated. The residue was crystallized from diethyl ether, to give the title compound (4.8 g, 54%) as pale brown crystals.

1. filtrationthis mixture was filtered through Celite
2. extractionthe residue was extracted with ethyl acetate
3. dry with materialThe organic layer was dried over magnesium sulfate
4. customthe residue was purified by silica gel column chromatography (eluted with ethyl acetate:n-hexane=1:1)
5. concentrationthe objective fractions were concentrated
6. customThe residue was crystallized from diethyl ether

ORD record

ord-fd56428ed3514e00841eda70035b99ec

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06841549B1