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-48a9f1d1db144b28998389b707bf3391

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129391B2