HCID 22125024, compound → HCID 22125082, compound

HRID 1858242Notes

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:19][CH3:20])=[N:15][CH:16]=2)[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][CH2:28]Cl)[CH:22]=2)[C:10]1=[O:30].[K].[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12>CN(C)C=O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([S:19][CH3:20])=[N:15][CH:16]=2)[N:11]([C:21]2[CH:26]=[CH:28][CH:27]=[C:23]([CH2:24][CH2:25][N:36]3[C:35](=[O:37])[C:34]4=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]4[C:32]3=[O:42])[CH:22]=2)[C:10]1=[O:30]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 0.5 g (1.1 mmol) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydro-1-(3-(2-chloroethyl)phenyl)pyrimido[4,5-d]pyrimidin-2(1H)-one in 30 ml of dimethylformamide was treated with 0.2 g (1.1 mmol) of phthalimide potassium salt and the mixture was heated at 80° C. for 2 hours. The cooled mixture was evaporated and partitioned between 40 ml of dichloromethane and 40 ml of water. The organic phase was dried over magnesium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel using diethyl ether/hexane (1:1) for the elution. Product-containing fractions were combined and evaporated to give 0.43 g (70%) of 3-(2,6-dichlorophenyl)-7-methylthio-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =590].

Workup

customThe cooled mixture was evaporated
custompartitioned between 40 ml of dichloromethane and 40 ml of water
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered
customevaporated
washfor the elution
customevaporated

Sources & evidence

ORD record: ord-b9b3cd3d58684373aba1014b77419b23
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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