4-(2-(Diethylamino)ethoxy)aniline → HCID 22125170, compound

HRID 1858186Notes

Reaction equation

HRID 1858186 reaction equation
[C: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])[CH:6]=[CH:5][CH:4]=[CH:3][CH: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]>>[C: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])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22124997HCID 22124997, compound

Product 1

HCID 22125170HCID 22125170, compoundYield 10.1%

Conditions

Temperature
175 °C

Procedure

A mixture of 100 mg (0.31 mmol) of 3-phenyl-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 170-180° C. for 10 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 sodium bicarbonate solution, dried over magnesium sulfate, filtered and evaporated. The residual solid was purified by crystallisation from cyclohexane/ethyl acetate to give 14 mg (10%) of 3-phenyl-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 141-144° 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 sodium bicarbonate solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residual solid was purified by crystallisation from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-e4dc750aa3384ceaa0a9c30a9ff68074
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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