Aniline → 3-(2,6-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-isopropylpyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858223Notes

Reaction equation

HRID 1858223 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]([CH:23]([CH3:25])[CH3:24])[C:10]1=[O:26].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.ClCCl.CO.[C:39]([OH:42])(=O)[CH3:40].O>>[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:27][C:28]3[CH:33]=[CH:32][C:31]([O:42][CH2:39][CH2:40][N:9]([CH2:18][CH3:17])[CH2:3][CH3:2])=[CH:30][CH:29]=3)=[N:15][CH:16]=2)[N:11]([CH:23]([CH3:25])[CH3:24])[C:10]1=[O:26]

Participants

4

Reactant 3

HCID 6115AnilineHCID 18914200Dichloromethane methanol acetic acid waterHCID 221249913-(2,6-dichlorophenyl)-1-isopropyl-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 221251293-(2,6-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-isopropylpyrimido[4,5-d]pyrimidin-2(1H)-oneYield 22%

Conditions

Temperature
180 °C

Procedure

A mixture of 70 mg (0.16 mmol) of 3-(2,6-dichlorophenyl)-1-isopropyl-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one and 166 mg (0.8 mmol) of 4-[2-diethylamino)ethoxy]aniline was heated at 180° C. for 35 minutes and then cooled. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined and evaporated and the residue was evaporated with toluene. The residue was then dissolved in 30 ml of dichloromethane, washed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time, dried over magnesium sulfate, filtered and evaporated to give 5 mg (22%) of 3-(2,6-dichlorophenyl)-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydro-1-isopropylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 125° C.

Workup

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was then dissolved in 30 ml of dichloromethane
  6. washwashed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-227733ca387e46e29b9a6c3ef71c0567
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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