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Chapter 1
Synthesis of functionalized pyrimidines
General synthetic procedure for the 2-chloropyrimidine derivatives
(ASM-03a-e).
In a 50mL round bottom flask equipped with magnetic stirrer and thermometer
was placed ASM-02a-e (10 mmol) and POCl 3 (15 mL). Reaction mixture heated up to
reflux temperature and maintain for 2-3 hrs. The progress of reaction was monitored
by thin layer chromatography. After completion of reaction, the mixture was poured
in to crushed ice and neutralized with saturated sodium bicarbonate solution. The
products was filtered, washed with water and dried. Crystallize crude product from
methanol and used for next step without further purification.
General synthetic procedure for the 2-substitutedpyrimidine derivatives
via Suzuki-Miyaura coupling (ASM-03a-e).
A mixture of 2-choropyrimidine derivatives ASM-03a-e (1.0 mmol) and
phenylboronicacid derivatives (1.2 mmol) in 1,4-dioxane (12 mL) was stirred for 10
min at rt. To this mixture, saturated solution of K 2 CO 3 (8 mL) was added followed by
tetrakis(triphenylphosphine)palladium(0) (5 mol%). The reaction mixture was heated
at 110 o C for 5-8 hrs. After completion, the reaction mixture was cooled to room
temperature, diluted with ethyl acetate and filtered through pad of celite. The filtrate
was washed with water (2 x 100 mL) and brine solution (100 mL). The organic layer
was separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was
evaporated to dryness under vacuo. The residue was purified by using column
chromatography using EtOAc/Ether (0.5:9.5) to afford analytically pure products
ASM-04a-e.
Department of Chemistry, Saurashtra University, Rajkot-360005 26