Potassium Iodide → 1,3-Dimethyl-6-(2-(tritylthio)ethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Temperature

50 °C

1,3-Dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione) (step 2)(10 g, 55.8 mmol), (2-chloroethyl)(trityl)sulfane (step 1) (20.81 g, 61.4 mmol), potassium iodide (1.853 g, 11.16 mmol) and caesium carbonate (36.4 g, 112 mmol) were suspended in anhydrous dimethylacetamide (250 mL), forming a dark orange suspension. The vessel was evacuated and back-filled with N2 (×3) and stirred under nitrogen at 50° C. for 41.7 h. The reaction was cooled to room temperature and decanted slowly into a stirring water (800 mL) and EtAcO (200 mL) mixture. The layers were separated and the aqueous extracted with EtOAc (4×100 mL). The solids present where collected by reduced pressure filtration (solid 1). The combined organics were washed with water (4×100 mL), brine (2×100 mL), dried (Na2SO4) and filtered under reduced pressure. The organic solvent was evaporated under reduced pressure to afford a pale yellow solid, which was suspended in Et2O (200 mL) and stirred at room temperature for 10 mins; the pale tan solid was then collected by reduced pressure filtration (solid 2). The solid collected from the extraction mixture (solid 1) was washed with water (100 mL), EtOAc (100 mL) and stirred in Et2O (100 mL) for 10 mins at room temperature and collected by reduced pressure filtration. Both solids were dried under vacuum at 50° C. for 16 h. Both crops were then blended to afford the title compound as a tan solid;

1. customforming a dark orange suspension
2. customThe vessel was evacuated
3. additionback-filled with N2 (×3)
4. temperatureThe reaction was cooled to room temperature
5. customdecanted slowly into a stirring water (800 mL) and EtAcO (200 mL) mixture
6. customThe layers were separated
7. extractionthe aqueous extracted with EtOAc (4×100 mL)
8. filtrationThe solids present where collected by reduced pressure filtration (solid 1)
9. washThe combined organics were washed with water (4×100 mL), brine (2×100 mL)
10. dry with materialdried (Na2SO4)
11. filtrationfiltered under reduced pressure
12. customThe organic solvent was evaporated under reduced pressure
13. customto afford a pale yellow solid, which
14. stirringstirred at room temperature for 10 mins
15. filtrationthe pale tan solid was then collected by reduced pressure filtration (solid 2)
16. customThe solid collected from the extraction mixture (solid 1)
17. washwas washed with water (100 mL), EtOAc (100 mL)
18. stirringstirred in Et2O (100 mL) for 10 mins at room temperature
19. filtrationcollected by reduced pressure filtration
20. customBoth solids were dried under vacuum at 50° C. for 16 h

ORD record

ord-edf13c06f2f64a3aaa6dbaa0f612c7fc

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359381B2