Methanol → Pyrimidine, 5-bromo-2-methoxy-

Sodium metal (74 mg, 3.10 mmol) was added in portions to CH3OH (25 mL) at 0° C. and the mixture was stirred for 30 min at RT. 5-Bromo-2-chloropyrimidine (500 mg, 2.58 mmol) was added to the above mixture at 0° C., and the resulting reaction mixture was gradually heated to reflux temperature and stirred for 2 h. After complete consumption of the starting material (by TLC), the volatiles were concentrated under reduced pressure; the residue was quenched with ice-cold water (50 mL) and extracted with EtOAc (2×50 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 S (400 mg). The crude material was used directly in the next step without any further purification.

1. customthe resulting reaction mixture
2. temperaturewas gradually heated
3. temperatureto reflux temperature
4. stirringstirred for 2 h
5. customAfter complete consumption of the starting material (by TLC)
6. concentrationthe volatiles were concentrated under reduced pressure
7. customthe residue was quenched with ice-cold water (50 mL)
8. extractionextracted with EtOAc (2×50 mL)
9. washThe combined organic extracts were washed with water (50 mL) and brine (50 mL)
10. dry with materialdried over anhydrous Na2SO4
11. concentrationconcentrated under reduced pressure
12. customto obtain the crude S (400 mg)
13. customThe crude material was used directly in the next step without any further purification

ORD record

ord-5dff5aea05d94c83b1f911f5e9e89761

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901121B2