Short access to 6-substituted pyrimidine derivatives by the S(RN)1 mechanism. Synthesis of 6-substituted uracils through a one-pot procedure.
The synthesis of 6-substituted 2,4-dimethoxypyrimidines with different nucleophiles was accomplished with good to excellent yields (50-95%) through S(RN)1 reactions, starting from commercially available 6-chloro-2,4-dimethoxypyrimidine (1). Hydrolysis of these derivatives gave access to 6-substituted uracils with good yields and short times by the use of microwave irradiation. The preparation of uracils from 1 without the isolation of 2,4-dimethoxypyrimidine derivatives affords a rapid access to these compounds in good yields and excellent purity by avoiding an unnecessary step of purification.
Bardagí
Javier I
JI
INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba, Argentina.
Rossi
Roberto A
RA
D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D011743:Pyrimidines / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014498:Uracil / Q000138:chemical synthesis* / Q000737:chemistry
D011743:Pyrimidines; D014498:Uracil