Sodium Bicarbonate → HCID 58882929, compound

To a solution of 5-bromo-2-methyl-pyridin-3-ylamine (Stage 75.1.4, 3.81 mmol) in THF (25 ml) cooled with an ice-bath was added 1 M bis(trimethylsilyl)amide in THF (4.38 mmol). The RM was stirred for 1 h at rt then was added iodomethane (4.38 mmol). The RM was stirred for 1 h at rt. The RM was cooled with an ice-bath and was added 1 M bis(trimethylsilyl)amide in THF (1.9 mmol). The RM was stirred for 30 min at it then was added iodomethane (1.9 mmol). The RM was stirred for 1 h at it then was diluted with EtOAc and washed with aqueous Na2CO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was taken in MeOH and separated by preparative HPLC. The first eluting pure fractions containing product were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined fractions were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a brown oil (HPLC: tR 1.88 min (Method A); M+H=201, 203 MS-ES). The second eluting pure fractions, that contained (5-bromo-2-methyl-pyridin-3-yl)-dimethyl-amine side product, were basified with NaHCO3, concentrated and extracted with dichloromethane (2×). The combined fractions were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a brown oil (HPLC: tR 2.01 min (Method A); M+H=215, 217 MS-ES).

1. concentrationconcentrated
2. extractionextracted with dichloromethane (2×)
3. washThe combined fractions were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated

ORD record

ord-b7464838c13941a0b7e53b937ff70fc9

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2