Sulfuric Acid → 8-phenyl-2-phenylamino-6-pyridin-3-yl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 11788Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:6][C:7]1[C:8]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:9][C:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:11][CH:12]=1)C.S(=O)(=O)(O)O>C(O)(=O)C.C(OCC)(=O)C>[C:21]1([N:20]2[C:8]3[N:9]=[C:10]([NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:11]=[CH:12][C:7]=3[CH2:6][CH:5]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[C:4]2=[O:3])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester (60 mg, 0.36 mmol) (from Example 10b supra) was added 5% concentrated sulfuric acid in glacial acetic acid (3 mL) in one portion. The reaction mixture was heated at 120° C. for 3 hours. The reaction mixture was then diluted with ethyl acetate (100 mL) and quenched with 2 N aqueous sodium hydroxide solution. The organic layer was separated and successively washed with water (30 mL) and brine (30 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 8-phenyl-2-phenylamino-6-pyridin-3-yl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one as a white solid. (Yield 37.3 mg, 69.3%).

Workup

customquenched with 2 N aqueous sodium hydroxide solution
customThe organic layer was separated
washsuccessively washed with water (30 mL) and brine (30 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-710b344f3c0a4faa858fdd396076bad7
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098332B2

Reaction notes

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