Dimethylamine → HCID 9939402, compound

HRID 1858312Notes

Reaction equation

HRID 1858312 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].[CH3:48][NH:49][CH3:50]>C(O)C>[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]([CH2:30][CH3:31])[CH2:32][CH3:33])=[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][N:49]([CH3:50])[CH3:48])[CH:35]=2)[C:10]1=[O:47]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 11399802HCID 11399802, compound

Product 1

HCID 9939402HCID 9939402, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

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 of Example 81(a) was treated with 3 ml of a 33% solution of dimethylamine in ethanol and the mixture heated at 50° C. for 3 hours. The mixture was cooled and evaporated. The product was purified by column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined, evaporated and the residue evaporated with toluene. The residue was then dissolved in 40 ml of dichloromethane, washed with 40 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated to afford 10 mg (22%) of 3-(2,4-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-[3-(2-(dimethylamino)ethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 92° C.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated
  3. customThe product was purified by column chromatography on silica gel
  4. washfor the elution
  5. customevaporated
  6. customthe residue evaporated with toluene
  7. dissolutionThe residue was then dissolved in 40 ml of dichloromethane
  8. washwashed with 40 ml of saturated aqueous sodium bicarbonate solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-1e7a47bfc82b4aeaa6345b8877db740a
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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