4-(2-(Diethylamino)ethoxy)aniline → HCID 22125159, compound

HRID 1858267Notes

Reaction equation

HRID 1858267 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(C)(=O)=O)=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][OH:30])[CH:23]=2)[C:9]1=[O:31].[CH2:32]([N:34]([CH2:45][CH3:46])[CH2:35][CH2:36][O:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1)[CH3:33]>>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:42][C:41]3[CH:40]=[CH:39][C:38]([O:37][CH2:36][CH2:35][N:34]([CH2:45][CH3:46])[CH2:32][CH3:33])=[CH:44][CH:43]=3)=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH2:29][OH:30])[CH:23]=2)[C:9]1=[O:31]

Participants

3

Reactant 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 22124978HCID 22124978, compound

Product 1

HCID 22125159HCID 22125159, compoundYield 18%

Conditions

Temperature
180 °C

Procedure

200 mg (0.40 mmol) of 3-(2-bromophenyl)-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]-7-methanesulfonyl-pyrimido[4,5-d]pyrimidin-2(1H)-one was treated with 250 mg (1.2 mmol) of 4-[2-(diethylamino)ethoxy]aniline and the mixture heated at 180° C. for 40 minutes. The mixture was cooled and the product purified by column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined, evaporated and the residue evaporated with toluene. The residue was 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 45 mg (18%) of 3-(2-bromophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-[3-(2-hydroxyethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 98° C.

Workup

  1. temperatureThe mixture was cooled
  2. customthe product purified by column chromatography on silica gel
  3. washfor the elution
  4. customevaporated
  5. customthe residue evaporated with toluene
  6. dissolutionThe residue was then dissolved 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-bd18a0cef29c4782acafd4522a21d5dd
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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