Aniline → HCID 21946023, compound

HRID 2216983Notes

Reaction equation

HRID 2216983 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9](=[O:23])[N:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH:11]([CH:12]([CH3:14])[CH3:13])[C:5]2=[CH:4][N:3]=1.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH:12]([CH:11]1[C:5]2[C:6](=[N:7][C:2]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[N:3][CH:4]=2)[N:8]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:9](=[O:23])[N:10]1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)([CH3:13])[CH3:14]

Participants

3

Reactant 2

HCID 6115AnilineHCID 21946007HCID 21946007, compound

Product 1

HCID 21946023HCID 21946023, compound

Conditions

Temperature
100 °C

Procedure

(±)-7-Chloro-4-isopropyl-3-(4-methoxy-phenyl)-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (22.0 mg; 0.054 mmol) (from Example 11d supra) and aniline (50 μL; 0.55 mmol) (Aldrich) were combined and heated in an oil bath at 100° C. for 1 hour. Upon cooling, the residue was triturated with hexanes and the supernatant was decanted off. The residue was dissolved in ethyl acetate and washed with water and then brine. The organic phase was mixed with silica gel, concentrated and subsequently purification by flash chromatography (Biotage 12M; 40:60 ethyl acetate-hexanes) and crystallization from dichloromethane-ether-petroleum ether gave (±)-4-isopropyl-3-(4-methoxy-phenyl)-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid. (Yield 14.8 mg; 59.1%). Melting Point: 229–235° C.

Workup

  1. temperatureUpon cooling
  2. customthe residue was triturated with hexanes
  3. customthe supernatant was decanted off
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. additionThe organic phase was mixed with silica gel
  7. concentrationconcentrated
  8. customsubsequently purification
  9. customby flash chromatography (Biotage 12M; 40:60 ethyl acetate-hexanes) and crystallization from dichloromethane-ether-petroleum ether

Sources & evidence

ORD record
ord-cfa7eb783cba4a3fadb9b7e0973b48c7
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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