ChemicalBook CAS DataBase List 3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylic acid

3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylic acid synthesis

5synthesis methods

Product Name:3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylic acid
CAS Number:1437323-26-6
Molecular formula:C14H13FN2O4
Molecular Weight:292.26

5-Pyrimidinecarboxylic acid, 3-(4-fluorophenyl)-1,2,3,4-tetrahydro-1-(1-methylethyl)-2,4-dioxo-, ethyl ester

1437323-27-7
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3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylic acid

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Yield: 84%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;water at 70; for 45 h;

Steps:

5.1.10 3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (7b)
4M HCl in 1,4-dioxane (30mL, 120mmol) and water (10mL) were added to ethyl 3-(4-fluorophenyl)-1-isopropyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (6b) (4.97g, 15.5mmol), and the reaction mixture was stirred at 70°C for 45h. The reaction mixture was cooled to room temperature, then concentrated. The residue was poured into water and the precipitate was collected by filtration, rinsed with water and dried to afford the title compound 7b as a white solid (3.81g, 13.0mmol, 84%). ¹H NMR (500MHz, CDCl₃): δ=1.47 (d, J=6.7Hz, 6H), 4.94 (spt, J=6.8Hz, 1H), 7.22 (d, J=6.7Hz, 4H), 8.57 (s, 1H), 12.34 (br s, 1H); ¹³C NMR (126MHz, CDCl₃): δ=21.6, 51.2, 102.1, 116.9 (d, J_CF=23.9Hz), 129.4, 129.9 (d, J_CF=10.1Hz), 148.1, 150.0, 163.0 (d, J_CF=250.7Hz), 163.3, 165.0; HRMS-ESI m/z [M+H]⁺ calcd. for C₁₄H₁₄FN₂O₄⁺: 293.0932, found: 293.0924.

References:

Inoue, Satoshi;Yamane, Yoshinobu;Tsukamoto, Shuntaro;Azuma, Hiroshi;Nagao, Satoshi;Murai, Norio;Nishibata, Kyoko;Fukushima, Sayo;Ichikawa, Kenji;Nakagawa, Takayuki;Hata Sugi, Naoko;Ito, Daisuke;Kato, Yu;Goto, Aya;Kakiuchi, Dai;Ueno, Takashi;Matsui, Junji;Matsushima, Tomohiro [Bioorganic and Medicinal Chemistry,2021,vol. 39,art. no. 116137]

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3-(4-fluorophenyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester

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