Iodobenzene → 2-Chloro-4-phenylpyrimidine

To a solution of iodobenzene (3.53 ml) in ether (10 ml) was added n-butyllithium (1.6M in hexane, 20 ml), and the mixture was stirred at room temperature for 20 minutes. The above solution was added to a solution of 2-chloropyrimidine (3.52 g) in ether (90 ml) at −30° C. The mixture was stirred at −30° C. for 30 minutes and then at 0° C. for 30 minutes, quenched with a solution of acetic acid (1.83 ml) and water (0.31 ml) in tetrahydrofuran (6 ml), and treated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (7.26 g) in tetrahydrofuran (30 ml). The mixture was stirred at 0° C. for 5 minutes, cooled to 0° C., treated with a cold aqueous solution of sodium hydroxide (3M, 9.2 ml), and stirred at 0° C. for 5 minutes. The organic phase was separated, washed with water and brine, dried over magnesium sulfate, concentrated and subjected to silica gel column chromatography (hexane-ethyl acetate, 7:3) to afford 2-chloro-4-phenylpyrimidine (3.39 g) as a solid.

1. stirringThe mixture was stirred at −30° C. for 30 minutes
2. waitat 0° C. for 30 minutes
3. customquenched with a solution of acetic acid (1.83 ml) and water (0.31 ml) in tetrahydrofuran (6 ml)
4. additiontreated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (7.26 g) in tetrahydrofuran (30 ml)
5. stirringThe mixture was stirred at 0° C. for 5 minutes
6. temperaturecooled to 0° C.
7. additiontreated with a cold aqueous solution of sodium hydroxide (3M, 9.2 ml)
8. stirringstirred at 0° C. for 5 minutes
9. customThe organic phase was separated
10. washwashed with water and brine
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated

ORD record

ord-3a898d9e21f04eb9901a60c6c9c52b29

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06727245B2