4-(2-(Diethylamino)ethoxy)aniline → HCID 22125022, compound

HRID 1858251Notes

Reaction equation

HRID 1858251 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=3)[N:10]([CH3:22])[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1.[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>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13]([NH:34][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][N:26]([CH2:37][CH3:38])[CH2:24][CH3:25])=[CH:36][CH:35]=4)=[N:14][CH:15]=3)[N:10]([CH3:22])[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22125048HCID 22125048, compound

Product 1

HCID 22125022HCID 22125022, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 18914200Dichloromethane methanol acetic acid waterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.5 mmol) of 3-(3-bromophenyl)-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. 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 to give 30 mg (11%) of 3-(3-bromophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as an off-white solid of melting point 150° 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

Sources & evidence

ORD record
ord-987f008815664e868113a3fe7122373d
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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