Hydrochloric Acid → 3-(2,6-dichlorophenyl)-7-(4-fluoroanilino)-3,4-dihydro-1-methylpyrimido[4,5-d]-pyrimidin-2(1H)-one

HRID 1858204Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24].[F:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:30][C:29]3[CH:31]=[CH:32][C:26]([F:25])=[CH:27][CH:28]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 100 mg (0.26 mmol) of 3-(2,6-dichlorophenyl)-7-methane-sulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 0.25 ml (2.6 mmol) of 4-fluoroaniline was heated at 180° C. for 30 minutes and then cooled. 30 ml of ethyl acetate and 30 ml of 2M hydrochloric acid were added to the residue. The phases were separated and the organic phase was washed with 20 ml of brine, dried over magnesium sulfate, filtered and evaporated. The residue was chromatographed on silica gel using ethyl acetate/hexane (2:3) for the elution. Product-containing fractions were combined and evaporated to give 40 mg (37%) of 3-(2,6-dichlorophenyl)-7-(4-fluoroanilino)-3,4-dihydro-1-methylpyrimido[4,5-d]-pyrimidin-2(1H)-one as a light grey solid of melting point 208-211° C.

Workup

temperaturecooled
customThe phases were separated
washthe organic phase was washed with 20 ml of brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated
customThe residue was chromatographed on silica gel
washfor the elution
customevaporated

Sources & evidence

ORD record: ord-9a95f1209929457c9e03d9db3e5a1b8c
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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