4-(2-(Diethylamino)ethoxy)aniline → HCID 22125016, compound

HRID 1858226Notes

Reaction equation

HRID 1858226 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=2)[N:10]([CH3:22])[C:9]1=[O:23].[CH2:24]([N:26]([CH2:37][CH3:38])[CH2:27][CH2:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1)[CH3:25]>ClCCl.CO.C(O)(=O)C.O>[CH2:37]([N:26]([CH2:24][CH3:25])[CH2:27][CH2:28][O:29][C:30]1[CH:31]=[CH:32][C:33]([NH:34][C:13]2[N:12]=[C:11]3[N:10]([CH3:22])[C:9](=[O:23])[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[CH2:17][C:16]3=[CH:15][N:14]=2)=[CH:35][CH:36]=1)[CH3:38]

Participants

4

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22125019HCID 22125019, compound

Product 1

HCID 22125016HCID 22125016, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 18914200Dichloromethane methanol acetic acid waterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.6 mmol) of 3-(2-methylphenyl)-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 35 minutes and then cooled. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution combined and evaporated and the residue was evaporated with toluene. The residue was dissolved in 30 ml of dichloromethane, washed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time, dried over magnesium sulfate, filtered and evaporated to give 30 mg (11%) of 7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-methyl-3-(2-methylphenyl)pyrimido[4,5-d]pyrimidin-2(1H)-one as a pink solid of melting point 132° C.

Workup

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was dissolved in 30 ml of dichloromethane
  6. washwashed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-31b804fad6744da9bbd7b0395d4f20c7
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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