Trimethylsilyldiazomethane → Methyl 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylate

(Trimethylsilyl)diazomethane, 2M in hexanes (4.19 ml, 8.38 mmol) was added dropwise to 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylic acid (1.28 g, 4.19 mmol) in toluene (12 ml) and methanol (3.00 ml) at 25° C. over a period of 2 mins under nitrogen. The resulting solution was stirred at ambient temperature for 2 hours. The reaction mixture was quenched with the dropwise addition of acetic acid until bubbling ceased, then the reaction mixture was diluted with EtOAc (100 mL) and water (100 mL). The organic layer was removed and the aqueous further extracted with EtOAc (2×50 mL). The combined organics were washed with sodium hydrogen carbonate solution (100 mL), water (100 mL), brine (100 mL) and dried over MgSO4, filtered and evaporated to afford methyl 2-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrimidine-5-carboxylate (1.182 g, 88%) as a yellow solid. This was used directly with no further purification.

1. customThe reaction mixture was quenched with the dropwise addition of acetic acid
2. customuntil bubbling
3. additionthe reaction mixture was diluted with EtOAc (100 mL) and water (100 mL)
4. customThe organic layer was removed
5. extractionthe aqueous further extracted with EtOAc (2×50 mL)
6. washThe combined organics were washed with sodium hydrogen carbonate solution (100 mL), water (100 mL), brine (100 mL)
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated

ORD record

ord-13711a9d963b4b229f251a04831ca191

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604022B2