Acetic Acid → HCID 11744580, compound

HRID 11771Notes

Reaction equation

CO[C:3](=[O:36])[CH:4]([C:26]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[CH:27]=1)[CH2:5][C:6]1[C:7]([NH:19]C2C=CC=CC=2)=[N:8][C:9]([NH:12]C2C=CC=CC=2)=[N:10][CH:11]=1.S(=O)(=O)(O)O.[C:42](O)(=O)[CH3:43]>C(OCC)(=O)C>[CH3:35][O:34][C:28]1[CH:27]=[C:26]([CH:4]2[C:3](=[O:36])[N:19]([C:43]3[CH:42]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:7]3[N:8]=[C:9]([NH:12][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:10]=[CH:11][C:6]=3[CH2:5]2)[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(3,5-dimethoxy-phenyl)-propionic acid methyl ester (0.11 mg, 0.23 mmol) (from Example 3c supra) in glacial acetic acid (2 mL) was added concentrated sulfuric acid (0.1 mL) in one portion. The reaction mixture was heated at 120° C. overnight. The reaction mixture was then diluted with ethyl acetate (50 mL) and quenched with 2 N aqueous sodium hydroxide solution. The organic layer was separated and successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude product which was crystallized from ethyl acetate-hexanes to give 6-(3,5-dimethoxy-phenyl)-8-phenyl-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as light brown solid. (Yield 73.3 mg, 71.4%).

Workup

customquenched with 2 N aqueous sodium hydroxide solution
customThe organic layer was separated
washsuccessively washed with water (10 mL) and brine (10 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give the crude product which
customwas crystallized from ethyl acetate-hexanes

Sources & evidence

ORD record: ord-71202caef48949bf8ff4e43739e43746
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098332B2

Reaction notes

Loading…