Bromine → 4-BROMOMETHYL-2-METHYLTHIOPYRIMIDINE

Temperature

80 °C

To a solution of 4-methyl-2-methylthiopyrimidine (12.6 g, 0.09 mol) in acetic acid (50.0 mL) was added bromine (5.5 mL, 0.11 mol) and heated at 80° C. under argon atmosphere for 2 h. Acetic acid was distilled in vacuo, the residue was triturated with dichloromethane (100.0 mL) and poured into satd. sod.bicarbonate solution (200.0 mL). Additional dichloromethane (100.0 ml) was added and stirred for 15 min. The organic phase was washed with water (3×100 mL), dried (Na2SO4), and concentrated under reduced pressure. The dark colored residue was purified by flash chromatography (EtOAc/hexane 1:4 v/v) to afford 4-(bromomethyl)-2-(methylthio)pyrimidine (10.9 g, 55%) as a dark colored liquid: 1H NMR (CDCl3/400 MHz) δ8.50 (d, 1H, J=4.8 Hz), 7.09 (d, 1H, J=4.8 Hz), 4.34 (s, 2H), and 2.56 (s, 3H); ESMS m/z 219 (M+H).

1. distillationAcetic acid was distilled in vacuo
2. customthe residue was triturated with dichloromethane (100.0 mL)
3. additionpoured into satd
4. additionAdditional dichloromethane (100.0 ml) was added
5. washThe organic phase was washed with water (3×100 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure
8. customThe dark colored residue was purified by flash chromatography (EtOAc/hexane 1:4 v/v)

ORD record

ord-7fca56364ba2469a903be36c33d33d5f

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07629363B2