4-(2-(Diethylamino)ethoxy)aniline → HCID 22125189, compound

HRID 1858246Notes

Reaction equation

HRID 1858246 reaction equation
[CH:1]([N:4]1[CH2:13][C:12]2[C:7](=[N:8][C:9](S(C)(=O)=O)=[N:10][CH:11]=2)[N:6]([CH3:18])[C:5]1=[O:19])([CH3:3])[CH3:2].[CH2:20]([N:22]([CH2:33][CH3:34])[CH2:23][CH2:24][O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)[CH3:21]>ClCCl.CO.C(O)(=O)C.O>[CH2:33]([N:22]([CH2:20][CH3:21])[CH2:23][CH2:24][O:25][C:26]1[CH:27]=[CH:28][C:29]([NH:30][C:9]2[N:8]=[C:7]3[N:6]([CH3:18])[C:5](=[O:19])[N:4]([CH:1]([CH3:3])[CH3:2])[CH2:13][C:12]3=[CH:11][N:10]=2)=[CH:31][CH:32]=1)[CH3:34]

Participants

4

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22125100HCID 22125100, compound

Product 1

HCID 22125189HCID 22125189, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 18914200Dichloromethane methanol acetic acid waterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 350 mg (1.2 mmol) of 3-isopropyl-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 500 mg (2.4 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. Product-containing fractions were combined and evaporated and the residue was 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. The residue was triturated in hexane, filtered off and dried to give 40 mg (8%) of 7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-3-isopropyl-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 154° C.

Workup

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was then dissolved in 40 ml of dichloromethane
  6. washwashed with 40 ml of saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was triturated in hexane
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-e9d1bf0777de49df9abdfc8d06364607
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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