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

HRID 2216964Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of (±)-3-[7-chloro-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile (0.49 g; 1.21 mmol) (from Example 5a supra) and aniline (0.50 mL; 5.49 mmol) (Aldrich) was heated to 110° C. for one hour. Methanol was added to the hot mixture and the solution was then cooled. The solid that precipitated out of solution was collected and recrystallized from methanol to yield (±)-3-[3-(4-methoxy-phenyl)-4-methyl-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile as a white solid. (Yield 0.35 g; 62.2%). Melting Point: 224–228° C.

Workup

temperaturethe solution was then cooled
customThe solid that precipitated out of solution
customwas collected
customrecrystallized from methanol

Sources & evidence

ORD record: ord-e8268c94ef07436e8f21db3394236bd5
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07112676B2

Reaction notes

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