2-Propyn-1-ol, 3-(5-pyrimidinyl)- (9CI) synthesis

Yield:174456-28-1 68%

Reaction Conditions:

with (4-nitrophenyl)(phenyl)methanone;palladium diacetate;potassium carbonate in N,N-dimethyl-formamide at 60; for 24 h;Inert atmosphere;Irradiation;

Steps:

2.2. General procedure for the Sonogashira-Hagihara reaction

General procedure: Aryl halide (0.5 mmol) and terminal alkyne (0.75 mmol) were addedto a 10 mL flask containing Pd(OAc)2 (0.2 mol%), K2CO3 (0.75 mmol,104 mg), p-nitrobenzophenone (10 mol%, 11 mg) and 1.5 mL DMF. Thereactant was irradiated under a 10 W blue LED (465 nm) for aryl iodides(25 C) and aryl bromides (25-60 C). The progress of the reactions wasmonitored by gas chromatography (GC). After completion of the reaction,distilled water (2 mL) was added to the reaction mixture and thecrude product was extracted with ethyl acetate (3 × 3.0 mL). The crudeproduct was further purified by column or plate chromatography usinghexane and ethyl acetate as eluents.

References:

Firouzeh, Ebrahim;Kazemi, Foad;Gholinejad, Mohammad;Kaboudin, Babak [Journal of Photochemistry and Photobiology A: Chemistry,2022,vol. 431,art. no. 114002]