5-Bromo-2-iodopyrimidine → HCID 89810846, compound

Temperature

-78 °C

5-Bromo-2-iodopyrimidine (2 g, 7.02 mmol) was dissolved in dry toluene (30 mL) and cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 2.95 mL) was added dropwise, and the reaction mixture was aged for 30 minutes prior to dropwise addition of oxetan-3-one (0.452 mL, 7.72 mmol). The reaction mixture was stirred at −78° C. for 30 minutes, then allowed to warm to room temperature for 1 h. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were successively washed with water and brine, then dried over magnesium sulphate and filtered. The solvent was removed under reduced pressure. The resulting crude brown oily solid was absorbed onto a 25 g KP-Sil Biotage column with minimal DCM, and eluted using a Biotage Isolera 4 with 10-100% ethyl acetate in heptanes, to afford the title compound (687 mg, 42%) as a crystalline yellow solid. δH (500 MHz, DMSO-d6) 9.07 (s, 2H), 6.43 (s, 1H), 4.94 (d, J 6.5 Hz, 2H), 4.67 (d, J 6.5 Hz, 2H).

1. temperatureto warm to room temperature for 1 h
2. extractionextracted with ethyl acetate (3×100 mL)
3. washThe combined organic extracts were successively washed with water and brine
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. customThe solvent was removed under reduced pressure
7. customThe resulting crude brown oily solid was absorbed onto a 25 g KP-Sil Biotage column with minimal DCM
8. washeluted

ORD record

ord-e68c0b812d8844a68de4a6801b4d9495

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2