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) δ 8.50 (d, 1H, J=4.8 Hz), 7.09 (d, 1H, J=4.8 Hz), 4.34 (s, 2H), and 2.56 (s, 3H); ES MS 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-64ca195812b14eb392ca46273d6d5e0d

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067540B2