Diphosgene → 3-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)-5-nitrobenzonitrile

HRID 599277Notes

Reaction equation

HRID 599277 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[CH:9]([NH:12][C:13]1[C:18]([CH2:19][NH:20][C:21]2[CH:22]=[C:23]([CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=2)[C:24]#[N:25])=[CH:17][N:16]=[C:15]([S:32][CH3:33])[N:14]=1)([CH3:11])[CH3:10]>CCN(CC)CC>[CH:9]([N:12]1[C:13]2=[N:14][C:15]([S:32][CH3:33])=[N:16][CH:17]=[C:18]2[CH2:19][N:20]([C:21]2[CH:22]=[C:23]([CH:26]=[C:27]([N+:29]([O-:31])=[O:30])[CH:28]=2)[C:24]#[N:25])[C:4]1=[O:3])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 67063031HCID 67063031, compound

Product 1

HCID 670631623-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)-5-nitrobenzonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Diphosgene (5 mL, 41 mmol), 3-((4-(isopropylamino)-2-(methylthio)pyrimidin-5-yl)methylamino)-5-nitrobenzonitrile (2.2 g, 6.15 mmol) and Et3N (2.5 mL) were combined by the procedure of Example A4 step 3 to give 3-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)-5-nitrobenzonitrile (1.2 g, 51% yield), which was used in the next step without further purification.

Sources & evidence

ORD record
ord-8dd53af33148478d92d44fba5d91a832
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…