ChemicalBook CAS DataBase List 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester synthesis

7synthesis methods

Product Name:4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester
CAS Number:917392-54-2
Molecular formula:C18H16N4O2
Molecular Weight:320.35

104901-43-1
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66521-66-2 Synthesis

66521-66-2
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4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester

917392-54-2
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Yield:917392-54-2 81%

Reaction Conditions:

with chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II);caesium carbonate in 1,4-dioxane at 120; for 1.5 h;Inert atmosphere;

Steps:

Preparation of Intermediate INT-A
To a solution of 4-(pyridin-3-yl)pyrimidin-2-amine (2 g, 11.62 mmol, 1.00 equiv) and methyl 3-bromo-4-methylbenzoate (2.92 g, 12.75 mmol, 1.10 equiv) in dioxane (20 mL) were added CS2CO3 (5.3 g, 16.27 mmol, 1.40 equiv) and BrettPhos precatalyst (32 mg, 0.04 mmol, 0.03 equiv). The flask was evacuated and flushed three times with nitrogen. The resulting solution was stirred for 1.5 h at 120 °C. The reaction mixture was cooled to 20 °C. The resulting solution was diluted with EtOAc (50 mL). The solids were filtered out. The filtrate was washed with brine (3 x 30 mL). The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was washed with ethyl acetate/petroleum ether (1 :3). The solid was collected by filtration to afford 3.0 g (81%) of methyl 4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate as an off-white solid. NMR (400 MHz, CDCh) δ: 9.33-9.34 (m, 1H), 9.03-9.04 (m, 1H), 8.75-8.77 (m, 1H), 8.59-8.45 (m, 2H), 7.74-7.77 (m, 1H), 7.46-7.50 (m, 1H), 7.35-7.23 (m, 1H), 7.11 (s, 1H), 3.98 (s, 3H), 2.44 (s, 3H).

References:

AUSPEX PHARMACEUTICALS, INC.;ZHANG, Chengzhi;LAUFER, Ralph WO2018/106850, 2018, A1 Location in patent:Paragraph 00106

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18595-18-1 Synthesis