Ammonia → HCID 58092735, compound

6.69 g (74.7 mmol) copper(I)cyanide in 15 ml dry THF was cooled to −75° C., where 149 ml (149 mmol) of a 1M tert-butylmagnesium chloride solution was added drop-wise. Stirring was continued for 40 min. After that, 4.07 g (18.67 mmol) 2-bromo-5-methoxymethoxy-pyridine (Zhong, W. et al. WO2008147547) dissolved in 30 ml dry THF were added drop-wise. The reaction mixture was stirred at −75° C. for 1 h and then allowed to reach room temperature, where stirring was continued for another 6 h. Then 30 ml of 25% aqueous ammonia was added to the reaction mixture. The mixture was filtered and extracted twice with CH2Cl2. The combined organic layers were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel (EtOAc, heptane) to yield 2.64 g of the pure title compound as an oil. LCMS: tR=0.55 min, M+H=196 (method K).

1. additionwere added drop-wise
2. stirringThe reaction mixture was stirred at −75° C. for 1 h
3. customto reach room temperature
4. stirringwhere stirring
5. waitwas continued for another 6 h
6. filtrationThe mixture was filtered
7. extractionextracted twice with CH2Cl2
8. washThe combined organic layers were washed with water
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by chromatography on silicagel (EtOAc, heptane)

ORD record

ord-650908670b2c4181a7fcb27627776ddc

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357707B2