The addition of β-ketoacids to 4-(trifluoromethyl)pyrimidin- 2(1Н)-ones with decarboxylation: an effective method for the synthesis of 4-(2-oxoalkyl)-6-(trifluoromethyl)-3,4-dihydropyrimidin-2-ones

Substituent-Driven Selective N-/O-Alkylation of 4-(Trihalomethyl)pyrimidin-2(1H)-ones Using Brominated Enones

“…Several derivatization techniques have already been reported for the synthesis of trihalomethyl (−CCl 3 or −CF 3 ) pyrimidines, − with the most widely explored derivatization technique being alkylation (usually N - or O -) using alkyl halides or esters . However, the selectivity of the reaction (to furnish N - or O -alkylated products) in the absence of protecting groups or catalysts is still a problem .…”

“…White solid (582 mg, 75% yield), mp 166−168 °C 1. H NMR (600 MHz, DMSO-d 6 ): δ (ppm)14.01 (brs, 1H), 8.33 (d, 2H, J = 8.5 Hz), 8.23 (s, 1H), 7.64 (d, 1H, J = 7.2 Hz), 7.58 (t, 2H, J = 7.5 Hz), 6.85 (s, 1H), 5.62 (s, 2H) 13. C{ 1 H} NMR (150 MHz, DMSO-d 6 ): δ (ppm) 169.1, 164.5, 157.3 (q, 2 J C−F = 35.3 Hz), 141.4 (q, 2 J C−F = 36.9 Hz), 139.9, 134.7, 132.7, 129.3, 128.0, 121.8 (q, 1 J C−F = 268.0 Hz), 120.6 (q, 1 J C−F = 275.2 Hz), 107.5, 104.2, 59.8 19.…”

Chemoselective O-Alkylation of 4-(Trifluoromethyl)pyrimidin-2(1H)-ones Using 4-(Iodomethyl)pyrimidines

“…There have been several studies regarding the chemoselectivity between N - and O -alkylation − (or S -alkylation in pyrimidine-2­(1 H )-thiones − ) when preparing alkyl/aryl derivatives; however, directing the reaction toward furnishing one sole product in the absence of protecting groups or specific catalysts is a problem yet to overcome . More specifically, several derivatization techniques have already been reported for the synthesis of trifluoromethyl-containing pyrimidines; − however, the most widely explored one is still alkylation using alkyl halides or esters, and others are based on the application of TMS-protected pyrimidines, cyclocondensation strategies using starting materials that allow the desired substitution pattern, − and copper-mediated coupling reactions with aryl boronic acids …”