4-[2-(Dimethylamino)ethoxy]aniline → HCID 22125049, compound

HRID 1858206Notes

Reaction equation

HRID 1858206 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl: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].[CH3:25][N:26]([CH3:37])[CH2:27][CH2:28][O:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:34][C:33]3[CH:32]=[CH:31][C:30]([O:29][CH2:28][CH2:27][N:26]([CH3:37])[CH3:25])=[CH:36][CH:35]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

3

Reactant 2

HCID 64846554-[2-(Dimethylamino)ethoxy]anilineHCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125049HCID 22125049, compoundYield 23%

Conditions

Temperature
160 °C

Procedure

A mixture of 200 mg (0.52 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 140 mg (0.8 mmol) of 4-[2-(dimethylamino)ethoxy]aniline was heated at 160° C. for 2 hours and then cooled. The residue was chromatographed on silica gel using firstly dichloromethane/methanol/acetic acid/water (240:24:3:2) and then dichloromethane/methanol/acetic acid/water (90:18:3:2) for the elution. Product-containing fractions were combined and evaporated. The residue was evaporated with toluene and 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 35 mg (23%) of 3-(2,6-dichlorophenyl)-7-[4-[2-(dimethylamino)ethoxy]anilino]-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 173-174° C.

Workup

  1. temperaturecooled
  2. customThe residue was chromatographed on silica gel using firstly dichloromethane/methanol/acetic acid/water (240:24:3:2)
  3. washdichloromethane/methanol/acetic acid/water (90:18:3:2) for the elution
  4. customevaporated
  5. customThe residue was evaporated with toluene
  6. dissolutiondissolved 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-d1753c0a371f413eb3190c366559b693
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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