Methanol → 1-Ethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Temperature

-40 °C

A suspension of 5-formyluracil (0.84 g, 6.0 mmol) in anhydrous dimethylformamide (12 mL) under a nitrogen atmosphere was cooled to −40° C. The reaction mixture was treated with sodium hydride (60% mineral oil dispersion, 0.26 g, 6.6 mmol), stirred 30 min., then treated with iodoethane (0.53 mL, 6.6 mmol). The mixture warmed to 20° C. over 3 h., then was brought to 40° C. for 48 h. At this time the reaction mixture was cooled to room temperature, treated with methanol (5 mL) and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel eluted with a gradient of ethyl acetate in hexanes (1:3 to 1:2 to 1:1) to leave the product (0.25 g) as a white powder. MS (ESI-POS): [M+H]+=169.

1. temperatureThe mixture warmed to 20° C. over 3 h.
2. waitwas brought to 40° C. for 48 h
3. temperatureAt this time the reaction mixture was cooled to room temperature
4. customevaporated to dryness under reduced pressure
5. customThe residue was purified by chromatography on silica gel
6. washeluted with a gradient of ethyl acetate in hexanes (1:3 to 1:2 to 1:1)

ORD record

ord-6511a747a3264db3a42048d72285619c

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582636B2