4-Pyrimidinecarboxylicacid,2-methyl-,ethylester(9CI) synthesis
- Product Name:4-Pyrimidinecarboxylicacid,2-methyl-,ethylester(9CI)
- CAS Number:76240-14-7
- Molecular formula:C8H10N2O2
- Molecular Weight:166.18
76240-19-2
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124-42-5
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76240-14-7
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Yield:76240-14-7 65%
Reaction Conditions:
with triethylamine in 1,4-dioxane at 100; for 48 h;Reagent/catalyst;Solvent;Temperature;
Steps:
General procedure for the preparation of esters 16 (method B)
General procedure: Et3N (27.9 mL, 20.2 g, 0.200 mol) was added to a stirred mixture of b-alkoxyvinyl ester 1-3 (0.100 mol) and the corresponding amidine/guanidine 4-15 (0.120 mol) in 1,4-dioxane (200 mL). The resulting mixture was stirred at 100 °C for 48 h, then cooled to rt and evaporated in vacuo. The residue was diluted with H2O (150 mL) and extracted with t-BuOMe (2x100 mL). The combined organic extracts were washed with water (50 mL), dried over Na2SO4, filtered through silica gel and evaporated in vacuo. Ethyl 2-methylpyrimidine-4-carboxylate 16{1,5} Yield 10.8 g (65%; Method A - 39%); brownish liquid. 1H NMR (400 MHz, CDCl3) d 8.81 (d, J 4.9 Hz, 1H), 7.74 (d, J 4.9 Hz, 1H), 4.44 (q, J 7.1 Hz, 2H), 2.80 (s, 3H), 1.38 (t, J 7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3) d 169.1, 164.3, 159.0, 155.2, 117.7, 62.6, 26.2, 14.2. LC/MS (CI): m/z 139 [MeH2C]CH(CH3)H], 167 [MH]. Anal.calcd. for C8H10N2O2: C, 57.82; H, 6.07; N, 16.86. Found: C, 57.94; H,5.68; N, 17.19.
References:
Stepaniuk, Oleksandr O.;Rudenko, Tymofii V.;Vashchenko, Bohdan V.;Matvienko, Vitalii O.;Kondratov, Ivan S.;Tolmachev, Andrey A.;Grygorenko, Oleksandr O. [Tetrahedron,2019,vol. 75,# 25,p. 3472 - 3478]
76240-19-2
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76240-14-7
35 suppliers
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