Uses
2-Methoxy-4-methylbenzaldehyde acts as a reagent in the synthesis of [3,2-d]pyrimidine derivatives as week as in the synthesis of tachykinin NK2 receptor antagonists which may be used in the treatment of IBS.
Synthesis Reference(s)
Journal of Medicinal Chemistry, 35, p. 734, 1992
DOI: 10.1021/jm00082a014
Synthesis
GENERAL METHODS: Potassium carbonate (K2CO3, 35 mg, 0.25 mmol) was added to a solution of anhydrous N,N-dimethylformamide (DMF, 6.0 mL) of 2-hydroxy-4-methylbenzaldehyde (34 mg, 0.25 mmol) and the mixture was stirred at room temperature for 30 min. Subsequently, iodomethane (CH3I, 30 μL, 68 mg, 0.5 mmol) was added and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, distilled water was added to terminate the reaction and the aqueous phase was extracted three times with ethyl acetate (EtOAc). The organic phases were combined and dried over anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography.
References
[1] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 734 - 746
[2] Synthesis (Germany), 2017, vol. 49, # 1,
