Aniline → HCID 10412291, compound

HRID 2216962Notes

Reaction equation

HRID 2216962 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[C:9](=[O:21])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:11]([CH3:12])[C:5]2=[CH:4][N:3]=1.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([N:8]2[C:6]3=[N:7][C:2]([NH:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:3][CH:4]=[C:5]3[CH:11]([CH3:12])[N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[C:9]2=[O:21])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 10409330HCID 10409330, compound

Product 1

HCID 10412291HCID 10412291, compound

Conditions

Temperature
100 °C

Procedure

The mixture of (±)-7-chloro-1,3-bis-(4-methoxy-phenyl)-4-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.30 g; 0.72 mmol) (from Example 4a supra) and aniline (0.20 mL; 2.16 mmol) (Aldrich) was heated at 100° C. for 40 minutes. The mixture was then cooled to room temperature and triturated with hexanes. The resulting solid was dissolved in dichloromethane, washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (Biotage, 12S, dichloromethane followed by 30:70 to 50:50 ethyl acetate-hexanes gradient) to give (±)-1,3-bis-(4-methoxy-phenyl)-4-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 0.303 g; 90.1%).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customtriturated with hexanes
  3. dissolutionThe resulting solid was dissolved in dichloromethane
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (Biotage, 12S, dichloromethane followed by 30:70 to 50:50 ethyl acetate-hexanes gradient)

Sources & evidence

ORD record
ord-77c66e929b4f4e84a41ddece92292cb8
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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