4-(2-(Diethylamino)ethoxy)aniline → HCID 22124990, compound

HRID 1858245Notes

Reaction equation

HRID 1858245 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24].[CH2:25]([N:27]([CH2:38][CH3:39])[CH2:28][CH2:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)[CH3:26]>ClCCl.CO.C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:35][C:34]3[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH2:28][N:27]([CH2:38][CH3:39])[CH2:25][CH3:26])=[CH:37][CH:36]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

4

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22125184HCID 22125184, compound

Product 1

HCID 22124990HCID 22124990, compoundYield 2.2%

Reagents, catalysts & solvents 1

HCID 18914200Dichloromethane methanol acetic acid waterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 160 mg (0.45 mmol) of 3-(2-chloro-6-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. Product-containing fractions were combined and evaporated and the residue was evaporated with toluene. The residue was then 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. The residue was purified further by HPLC. The mobile phase was water/0.1% trifluoroacetic acid (A) and acetonitrile/0.07% trifluoroacetic acid (B); the gradient was 5%-95% B over 20 minutes; and the product was detected using an ultraviolet detector at a wavelength of 215 nm. Product-containing fractions were lyophilized and the lyophilisate 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 5 mg (2%) of 3-(2-chloro-6-methylphenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a yellow gum. [Mass spectrum (ESI) MH+ =495].

Workup

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was then 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
  10. customThe residue was purified further by HPLC
  11. customover 20 minutes
  12. dissolutionthe lyophilisate was dissolved in 30 ml of dichloromethane
  13. washwashed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. customevaporated

Sources & evidence

ORD record
ord-10c5145c0ec44d10b577f48ff30b656f
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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