Chlorotrimethylsilane → HCID 46851255, compound

Temperature

125 °C

A flask was charged with 1-(2-cyano-3-methylbutanoyl)-3-ethylurea (1, 17.1 g, 87 mmol), HMDS (86 mL), and TMSCl (1.21 mL, 9 mmol). The reaction mixture is heated to reflux (125° C.) and left stirring for 16-24 h until solution became clear. Reaction is monitored by TLC and upon completion was cooled to room temperature then concentrated. To the resulting residue was added 1 vol. sat. NaHCO3 solution in dropwise. The mixture was added 4-5 vol. of water along with 4-5 vol. of EtOAc. An emulsion forms as the two layers are combined and the slurry is filtered, and the solid is filtered and washed with water (2×0.25 vol) to afford an off-white solid. These solids were dried in a vacuum oven overnight at 40 to 50° C. to yield 7.25 g (42.4%) of 1-ethyl-5-isopropyl-6-amino uracil 2.

1. temperatureThe reaction mixture is heated
2. waitleft
3. customReaction
4. temperaturewas cooled to room temperature
5. concentrationthen concentrated
6. additionTo the resulting residue was added 1 vol. sat. NaHCO3 solution in dropwise
7. additionThe mixture was added 4-5 vol. of water along with 4-5 vol. of EtOAc
8. filtrationthe slurry is filtered
9. filtrationthe solid is filtered
10. washwashed with water (2×0.25 vol)
11. customto afford an off-white solid
12. customThese solids were dried in a vacuum oven overnight at 40 to 50° C.

ORD record

ord-b30a0a1613c64020bd626ac4eac65a3a

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604193B2