4-(2-(Diethylamino)ethoxy)aniline → HCID 22125064, compound

HRID 1858188Notes

Reaction equation

HRID 1858188 reaction equation
[CH:1]1([N:7]2[CH2:16][C:15]3[C:10](=[N:11][C:12](S(C)(=O)=O)=[N:13][CH:14]=3)[N:9]([CH3:21])[C:8]2=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:23]([N:25]([CH2:36][CH3:37])[CH2:26][CH2:27][O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)[CH3:24]>>[CH:1]1([N:7]2[CH2:16][C:15]3[C:10](=[N:11][C:12]([NH:33][C:32]4[CH:31]=[CH:30][C:29]([O:28][CH2:27][CH2:26][N:25]([CH2:36][CH3:37])[CH2:23][CH3:24])=[CH:35][CH:34]=4)=[N:13][CH:14]=3)[N:9]([CH3:21])[C:8]2=[O:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22125068HCID 22125068, compound

Product 1

HCID 22125064HCID 22125064, compoundYield 18%

Conditions

Temperature
180 °C

Procedure

A mixture of 100 mg (0.31 mmol) of 3-cyclohexyl-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2-(1H)-one and 400 mg (1.9 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 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 40 ml of dichloromethane. The solution was 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 25 mg (18%) 3-cyclohexyl-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 90-92° C.

Workup

  1. temperaturecooled
  2. customThe residue was chromatographed on silica gel
  3. washfor the elution
  4. customevaporated
  5. customThe residue was evaporated with toluene
  6. dissolutiondissolved in 40 ml of dichloromethane
  7. washThe solution was washed with 40 ml of saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was triturated in hexane
  12. filtrationfiltered off
  13. customdried

Sources & evidence

ORD record
ord-2fce984800504b4ab0a66110d6335797
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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