Bromine → 4-Bromomethyl-5-propyl-6-chloro-pyrimidine
Reaction equation
[Br:1]Br.[CH2:3]([C:6]1[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=1[CH3:12])[CH2:4][CH3:5]>CC(O)=O>[CH2:3]([C:6]1[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=1[CH2:12][Br:1])[CH2:4][CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
Br2 (1.28 g, 8 mmol) is added dropwise to a stirred solution 101 in HOAc (20 ml) heated at 85° C. After addition, the mixture is stirred at 85° C. for 1 hour. The solvent is removed in vacuo and EtOAc (25 ml) and NaHCO3 (25 ml) are added to the residue. The layers are separated and the organic layer is washed with Na2S2O3 solution (sat. 15 ml) followed by brine (20 ml). The organic phase is dried (Na2SO4) and evaporated. The resulting yellow oil is purified by flash column (6:1 EtOAc, hexane) to afford the product (102) as a light yellow solid.