4-(2-(Diethylamino)ethoxy)aniline → HCID 22125183, compound

HRID 1858250Notes

Reaction equation

HRID 1858250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][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][C:5]([Cl:8])=[CH:4][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 22125086HCID 22125086, compound

Product 1

HCID 22125183HCID 22125183, compoundYield 6%

Conditions

Temperature
180 °C

Procedure

A mixture of 200 mg (0.52 mmol) of 3-(2,5-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 218 mg (1.04 mmol) of 4-(2-(diethylamino)ethoxy)aniline was heated at 180° C. for 30 minutes and then cooled. The residue was subjected to column chromatography on silica gel eluted with dichloromethane/methanol/acetic acid/water in a ratio of 240:24:3:2. Product containing fractions were combined, evaporated and the residue re-evaporated with toluene. The residue was dissolved in dichloromethane (40 ml), washed with saturated aqueous sodium bicarbonate (40 ml), dried over magnesium sulfate, filtered and evaporated to give 15 mg (6%) of 3-(2,5-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 138° C. [Mass spectrum (ESI) MH+ =514].

Workup

  1. temperaturecooled
  2. washeluted with dichloromethane/methanol/acetic acid/water in a ratio of 240:24:3:2
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe residue re-evaporated with toluene
  6. dissolutionThe residue was dissolved in dichloromethane (40 ml)
  7. washwashed with saturated aqueous sodium bicarbonate (40 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-bcb60cee34564a4ea49b7d0d57214703
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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