HCID 11399802, compound → HCID 22125156, compound

HRID 1858311Notes

Reaction equation

HRID 1858311 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[CH:22][CH:21]=3)=[N:15][CH:16]=2)[N:11]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41]OS(C)(=O)=O)[CH:35]=2)[C:10]1=[O:47].[C:48]1(=[O:58])[NH:52][C:51](=[O:53])[C:50]2=[CH:54][CH:55]=[CH:56][CH:57]=[C:49]12.[K]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH2:28][N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])=[CH:24][CH:25]=3)=[N:15][CH:16]=2)[N:11]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40][CH2:41][N:52]3[C:48](=[O:58])[C:49]4=[CH:57][CH:56]=[CH:55][CH:54]=[C:50]4[C:51]3=[O:53])[CH:35]=2)[C:10]1=[O:47]

Participants

4

Reactant 2

HCID 11399802HCID 11399802, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 22125156HCID 22125156, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 50 mg (0.07 mmol) of 3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino) ethoxy]anilino]-3,4-dihydro-1-[3-(2-methanesulfonyloxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one in 5 ml of dimethylformamide was treated with 17 mg (0.09 mmol) of potassium phthalimide and the mixture was heated at 90° C. for 1 hour. The mixture was cooled and evaporated. The residue was partitioned between 20 ml of ethyl acetate and 20 ml of water. The organic phase was dried over magnesium sulfate and evaporated to yield 50 mg (95%) of 3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =750].

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated
  3. customThe residue was partitioned between 20 ml of ethyl acetate and 20 ml of water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-73dc713a9da14e18b7bffbf06be51a43
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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