4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoic acid synthesis

13synthesis methods

Product Name:4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoic acid
CAS Number:945749-71-3
Molecular formula:C21H20N4O3
Molecular Weight:376.41

ethyl 4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoate

1056634-62-8
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4-(2-(4-MorpholinophenylaMino)pyriMidin-4-yl)benzoic acid

945749-71-3
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Yield:945749-71-3 100%

Reaction Conditions:

Stage #1: ethyl 4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)benzoatewith methanol;lithium hydroxide;water monomer in tetrahydrofuran; for 2 h;Heating / reflux;
Stage #2: with hydrogenchloride;water monomer in tetrahydrofuran;methanol;

Steps:

1

solution of ethyl 4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)benzoate (35.39 g, 87.6 mmol) in 3:1 methanol/tetrahydrofuran (350 mL) was treated with lithium hydroxide (4.41 g, 183.9 mmol) in water (90 mL). The mixture was heated at reflux for 2 h., cooled, concentrated and acidified with hydrochloric acid (2M, 92.5 mL, 185 mmol). The dark precipitate was filtered, washed with water, and dried under vacuum. The solid was ground to a powder with a mortar and pestle, triturated with methanol (500 mL) then filtered again to yield 4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)benzoic acid as a muddy solid. This material was washed with ether, air dried overnight, and ground to a fine powder with mortar and pestle. On the basis of mass recovery (34.49 g) the yield was assumed to be quantitative. ¹H NMR (300 MHz, J₆-DMSO) δ 9.47 (IH, s); 8.53 (IH, d, J= 5.2 Hz); 8.24 (2H, d, J= 8.5 Hz); 8.08 (2H, d, J= 8.8 Hz), 7.66 (2H, d, J = 9.1 Hz); 7.37 (IH, d, J= 5.2Hz); 6.93 (2H, d, J= 9.1 Hz); 3.73 (4H, m); 3.04 (4H, m). LC-ESI-MS (method C): rt 7.3 min.; m/z 377.1 [M+H]⁺.

References:

WO2008/109943,2008,A1 Location in patent:Page/Page column 57-58

247234-41-9 Synthesis