5-Bromopyrimidine → HCID 71143767, compound

To a stirred solution of 5-bromopyrimidine (0.45 g, 2.87 mmol) in Et2O (30 mL) was added n-BuLi (1.6 M in hexane; 1.8 mL, 2.87 mmol) at −78° C., and the mixture was stirred for 1 h under inert atmosphere. A solution of compound E (1.0 g, 2.87 mmol) in Et2O (10 mL) was added to the reaction mixture at −78° C., and stirring was continued for another 1 h. After complete consumption of the starting material (by TLC), the reaction mixture was quenched with satd NH4Cl solution (20 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude material. Purification by silica gel column chromatography (eluting with 40% EtOAc/hexanes) afforded 58 (0.16 g, 0.38 mmol, 13.3%) as a light yellow solid. 1H NMR (500 MHz, CDCl3): δ 9.10 (s, 1H), 8.80 (s, 2H), 8.55 (s, 1H), 8.06 (dd, J=8.5, 1.5 Hz, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.71-7.67 (m, 1H), 7.00 (br s, OH), 6.88-6.86 (m, 1H), 6.74-6.70 (m, 1H). MS (ESI): m/z 429 [M+H]+. HPLC: 98%.

1. stirringstirring
2. waitwas continued for another 1 h
3. customAfter complete consumption of the starting material (by TLC)
4. customthe reaction mixture was quenched with satd NH4Cl solution (20 mL)
5. extractionextracted with EtOAc (2×100 mL)
6. washThe combined organic extracts were washed with water (50 mL) and brine (50 mL)
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated under reduced pressure
9. customto obtain the crude material
10. customPurification
11. washby silica gel column chromatography (eluting with 40% EtOAc/hexanes)

ORD record

ord-8052e10e5eef4b679a341a1177449541

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221791B2