Aniline → (+/-)-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 2216986Notes

Reaction equation

HRID 2216986 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:9](=[O:22])[N:10]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=3[Cl:21])[CH:11]([CH3:12])[C:5]2=[CH:4][N:3]=1.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[Cl:21][C:14]1[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:13]=1[N:10]1[CH:11]([CH3:12])[C:5]2[C:6](=[N:7][C:2]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:3][CH:4]=2)[N:8]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]1=[O:22]

Participants

3

Reactant 2

HCID 6115AnilineHCID 10431977HCID 10431977, compound

Product 1

HCID 10344724(+/-)-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Conditions

Temperature
100 °C

Procedure

(±)-7-Chloro-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.20 g; 0.49 mmol) (from Example 12b supra) was combined with aniline (150 μL; 1.65 mmol) (Aldrich) and heated in an oil bath at 100° C. for about 70 minutes. Upon cooling, the residue was triturated with hexanes and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography (Biotage, 40M; 40:60 ethyl acetate-hexanes) to give (±)-3-(2-chloro-5-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a light yellow solid. (Yield 0.15 g; 63.7%).

Workup

  1. temperatureUpon cooling
  2. customthe residue was triturated with hexanes
  3. custompartitioned between ethyl acetate and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by flash chromatography (Biotage, 40M; 40:60 ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-5fe287b03b2d4683a7e9aa26c07cf77e
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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