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

HRID 1858203Notes

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

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 110 mg (0.29 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 0.31 ml (2.9 mmol) of benzylamine was heated at 180° C. for 10 minutes and then cooled. 30 ml of ethyl acetate and 30 ml of 2M aqueous hydrochloric acid were added to the residue. The phases were separated and the organic phase was washed in sequence with 20 ml of 5% aqueous sodium bicarbonate solution and 20 ml of brine, dried over magnesium sulfate, filtered and evaporated to give 93 mg (79%) of 7-benzylamino-3-(2,6-dichlorophenyl)-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 195-198° C.

Workup

temperaturecooled
customThe phases were separated
washthe organic phase was washed in sequence with 20 ml of 5% aqueous sodium bicarbonate solution and 20 ml of brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-6c618be5793340dd8a0a5b8de64f3f84
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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