Phosphorus oxychloride → 5-(2-Benzyloxy-ethyl)-4-chloro-6-methyl-pyrimidine
Reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:12](O)=[N:13][CH:14]=[N:15][C:16]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[C:12]([Cl:21])=[N:13][CH:14]=[N:15][C:16]=1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 160 (4.1 g, 17 mmol) and POCl3 (10 ml) is heated at 100° C. for 3 hours. The solvent is removed in vacuo and EtOAc (30 ml) and water (30 ml) are added to the residue. NaHCO3 (aq.) is carefully added until the pH of the aqueous layer is greater than 7. The layers are separated and the aqueous layer is extracted with EtOAc (2×30 ml). The combined extracts are washed with brine (50 ml), dried (Na2SO4) and solvent evaporated. Flash column purification of the residue (EtOAc:hexane=1:2) provides the product (161) as a light yellow oil.