Sodium hydride → HCID 63867546, compound

To a solution of N-2-hydroxyethylpyrrolidine (0.9 ml, 7.71 mmol) and 5-bromo-2-chloropyrimidine (1.2 g, 6.20 mmol), in DMF (7 ml), was added sodium hydride (60% in mineral oil, 0.35 g, 8.75 mmol). The mixture was stirred, under argon, at ambient temperature for 1 hour, before being heated to 90° C. and stirred for a further hour. The reaction mixture was then partitioned between ethyl acetate and water. The organics were separated, dried over magnesium sulfate and evaporated to dryness. The resultant oil was purified by flash chromatography on silica, eluting with an increasing gradient of methanol in dichloromethane (which contained 1% aqueous ammonia solution, 0.88 M) to give the title compound (640 mg, 38%); NMR Spectrum: (CDCl3) 1.76 (m, 4H), 2.39 (m, 4H), 3.90 (t, 2H), 4.48 (t, 2H), 8.50 (s, 2H); Mass Spectrum: M+H+ 272.

1. temperaturebefore being heated to 90° C.
2. stirringstirred for a further hour
3. customThe reaction mixture was then partitioned between ethyl acetate and water
4. customThe organics were separated
5. dry with materialdried over magnesium sulfate
6. customevaporated to dryness
7. customThe resultant oil was purified by flash chromatography on silica
8. washeluting with an increasing gradient of methanol in dichloromethane (which contained 1% aqueous ammonia solution, 0.88 M)

ORD record

ord-0844d7b57d664ae097e9cee74c7b12d9

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247562B2