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

HRID 2216960Notes

Reaction equation

HRID 2216960 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:22]3[CH:27]=[CH:26][CH:25]=[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.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH:11]([CH3:12])[C:5]3[C:6](=[N:7][C:2]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[N:3][CH:4]=3)[N:8]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:9]2=[O:21])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 10045358HCID 10045358, compound

Product 1

HCID 9867727(+/-)-3-(4-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Conditions

Temperature
110 °C

Procedure

(±)-7-Chloro-3-(4-methoxy-phenyl)-4-methyl-1-phenyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.13 g; 0.33 mmol) (from Example 1e supra) was combined with aniline (100 μL; 1.10 mmol) (Aldrich). The mixture was heated to 110° C. A clear solution resulted upon heating and then a new solid precipitated out of solution. Reaction mixture was cooled to room temperature after 45 minutes. The residue was triturated with hexanes and then purified by flash chromatography (Biotage, 40M, 40:60 to 50:50 ethyl acetate-hexanes gradient) to give (±)-3-(4-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as an off-white solid, after crystallization from ethyl acetate-hexanes. (Yield 21.6 mg; 14.8%). A substantial amount of (±)-3-(4-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one adhered to the silica and was eluted with 50:50 ethyl acetate-methanol. (Yield 88 mg; 60%). Melting Point: 222–234° C.

Workup

  1. customA clear solution resulted
  2. temperatureupon heating
  3. customa new solid precipitated out of solution
  4. customReaction mixture
  5. temperaturewas cooled to room temperature after 45 minutes
  6. customThe residue was triturated with hexanes
  7. custompurified by flash chromatography (Biotage, 40M, 40:60 to 50:50 ethyl acetate-hexanes gradient)

Sources & evidence

ORD record
ord-7335b79baa1446aea57b5ef9becad008
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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