Ethanol → Ethyl 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylate

Temperature

80 °C

To a mixture of 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carbonitrile (27.4 g) and EtOH (200 mL) was added 4 M HCl/dioxane (200 mL), followed by stirring at 80° C. overnight. The reaction mixture was left to be cooled to room temperature and then concentrated under reduced pressure. To the residue were added EtOH (200 mL) and water (200 mL), followed by stirring. The precipitate was collected by filtration. To the obtained precipitate was added chloroform, followed by dissolving therein, and MgSO4, activated carbon (10 g), and basic silica gel (100 mL) were added thereto, followed by stirring. The mixture was filtered through Celite and then concentrated under reduced pressure to obtain ethyl 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylate (23.3 g).

1. waitThe reaction mixture was left
2. temperatureto be cooled to room temperature
3. concentrationconcentrated under reduced pressure
4. additionTo the residue were added EtOH (200 mL) and water (200 mL)
5. stirringby stirring
6. filtrationThe precipitate was collected by filtration
7. additionTo the obtained precipitate was added chloroform
8. dissolutionby dissolving
9. additionMgSO4, activated carbon (10 g), and basic silica gel (100 mL) were added
10. stirringby stirring
11. filtrationThe mixture was filtered through Celite
12. concentrationconcentrated under reduced pressure

ORD record

ord-e864ef9567fd4aa892c815a713bed87e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051339B2