4-(2-(Diethylamino)ethoxy)aniline → HCID 22125070, compound

HRID 1858179Notes

Reaction equation

HRID 1858179 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].[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]>>[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: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

3

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125070HCID 22125070, compoundYield 9.1%

Conditions

Temperature
180 °C

Procedure

A mixture of 2.55 g (6.6 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 7 g (34 mmol) of 4-[2-(diethylamino)ethoxy]-aniline was heated at 180° C. for 35 minutes and then cooled. The residue was chromatographed on silica gel using firstly 5% methanol in dichloromethane and then dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined and evaporated. The residue was evaporated with toluene and then dissolved in 150 ml of dichloromethane. The solution was washed with 100 ml of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to give 1.18 g (35%) of crude product. Purification by crystallisation from cyclohexane/ethyl acetate gave 310 mg (9%) of pure 3-(2,6-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 123-124° C.

Workup

  1. temperaturecooled
  2. customThe residue was chromatographed on silica gel using firstly 5% methanol in dichloromethane
  3. washdichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution
  4. customevaporated
  5. customThe residue was evaporated with toluene
  6. dissolutiondissolved in 150 ml of dichloromethane
  7. washThe solution was washed with 100 ml of saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customto give 1.18 g (35%) of crude product
  11. customPurification
  12. customby crystallisation from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-0b471e50ed8b41918463788dcf930ed3
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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