Sodium hydride → HCID 86619519, compound

To a solution of 4.24 g (0.042 mol) cyclopentanmethanol in 40 mL DMSO was added 1.74 g sodium hydride 55% in oil and the mixture was stirred at room temperature for 45 min. To the resulting solution was added 5.06 g (0.020 mol) 2-amino-3,5-dibromopyrazine and the mixture was stirred at room temperature for 20 h. To the resulting solution was added 1.0 g (0.011 mol) cyclopentanemethanol and the mixture was stirred at room temperature for 20 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase washed with water (3×) and brine, dried over magnesium sulfate, evaporated and the residue was purified by chromatography on silica gel with heptane:ethyl acetate=9:1 to 3:1 to yield 3.845 g of the title compound as yellow orange crystals melting at 78-79° C.

1. stirringthe mixture was stirred at room temperature for 20 h
2. stirringthe mixture was stirred at room temperature for 20 h
3. customThe reaction mixture was partitioned between water and ethyl acetate
4. customThe phases were separated
5. washthe organic phase washed with water (3×) and brine
6. dry with materialdried over magnesium sulfate
7. customevaporated
8. customthe residue was purified by chromatography on silica gel with heptane

ORD record

ord-8fbf63fd035f46578b9909d71d48e13e

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691863B2