Hydrochloric Acid → 2-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570691Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[O:12])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:15][CH:14]=3)[C:9]([S:25][CH3:26])=[N:8][C:7]=2[N:27]=1.Cl.N1C=CC=CC=1.Cl>CN(C)C=O>[CH3:26][S:25][C:9]1[N:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([F:23])([F:22])[F:24])=[CH:17][CH:18]=2)[C:11](=[O:12])[C:6]2[CH:5]=[CH:4][C:3](=[O:2])[NH:27][C:7]=2[N:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

7-Methoxy-2-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidin-4(3H)-one (1.55 g) and pyridine hydrochloride (3.1 g) were added to N,N-dimethylformamide (20 ml), and the mixture was stirred at 120° C. for 2 hr, and allowed to be cooled. The reaction mixture was poured into 0.5M hydrochloric acid (22 ml), and the white precipitate was collected by filtration, washed with water, and dissolved in tetrahydrofuran (30 ml). The solution was diluted with ethyl acetate (60 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (1.33 g) as a white solid.

Workup

temperatureto be cooled
filtrationthe white precipitate was collected by filtration
washwashed with water
dissolutiondissolved in tetrahydrofuran (30 ml)
additionThe solution was diluted with ethyl acetate (60 ml)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
washThe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-5928e5b72fd54d14a0e8d60415b13f9a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

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