4-(2-(Diethylamino)ethoxy)aniline → HCID 22125105, compound

HRID 1858306Notes

Reaction equation

HRID 1858306 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH2:19][C:18]2[C:13](=[N:14][C:15](S(C)(=O)=O)=[N:16][CH:17]=2)[N:12]([CH3:24])[C:11]1=[O:25].[CH2:26]([N:28]([CH2:39][CH3:40])[CH2:29][CH2:30][O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[CH3:27]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH2:19][C:18]2[C:13](=[N:14][C:15]([NH:36][C:35]3[CH:34]=[CH:33][C:32]([O:31][CH2:30][CH2:29][N:28]([CH2:39][CH3:40])[CH2:26][CH3:27])=[CH:38][CH:37]=3)=[N:16][CH:17]=2)[N:12]([CH3:24])[C:11]1=[O:25]

Participants

3

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22125079HCID 22125079, compound

Product 1

HCID 22125105HCID 22125105, compoundYield 17%

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.48 mmol) of 3-(2,4,6-trichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 300 mg (1.4 mmol) of 4-[2-(diethylamino)ethoxy]aniline was heated at 180° C. for 30 minutes. The mixture was cooled and the product 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 45 mg (17%) of 3-(2,4,6-trichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 142° C.

Workup

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

Sources & evidence

ORD record
ord-82d38f4faa2245c7b934f15bfbcd73ff
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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