Calcium Carbonate → 4-Amino-2,6-dimethyl-3-iodopyridine

Benzyltrimethylammonium dichloroiodate (6 g) was added to 4-amino-2,6-dimethylpyridine (2.1 g) and calcium carbonate (2.25 g) in dichloromethane/methanol (55 ml) (8:3 v/v) and the mixture was stirred for 16 hours. Solvent was removed by evaporation and the residue partitioned between 5% sodium metabisulphite solution and dichloromethane. The aqueous phase was separated and washed with dichloromethane. The aqueous phase was then basified with sodium carbonate and extracted with dichloromethane. The organic phase was washed with water, saturated sodium chloride solution and dried (MgSO4). Solvent was removed by evaporation and the residue purified by flash chromatography eluting with dichloromethane/methanol (9:1 v/v) to give 4-amino-2,6-dimethyl-3-iodopyridine (B) (1.7 g) as a light yellow solid, m.p. 103°-110° C.; NMR (CDCl3): 2.3(s,3H), 2.7(s,3H), 4.6(br s,2H), 6.3(s,1H); mass spectrum (chemical ionisation): 249 (M+H)+.

1. customSolvent was removed by evaporation
2. customthe residue partitioned between 5% sodium metabisulphite solution and dichloromethane
3. customThe aqueous phase was separated
4. washwashed with dichloromethane
5. extractionextracted with dichloromethane
6. washThe organic phase was washed with water, saturated sodium chloride solution
7. dry with materialdried (MgSO4)
8. customSolvent was removed by evaporation
9. customthe residue purified by flash chromatography
10. washeluting with dichloromethane/methanol (9:1 v/v)

ORDレコード

ord-8999635297044fc28e53e277a1217eb5

出典データセット

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05236937