Hydrochloric Acid → 3-amino-5-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)benzonitrile

HRID 599278Notes

Reaction equation

HRID 599278 reaction equation
[CH:1]([N:4]1[C:9]2=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=[C:8]2[CH2:7][N:6]([C:16]2[CH:17]=[C:18]([CH:21]=[C:22]([N+:24]([O-])=O)[CH:23]=2)[C:19]#[N:20])[C:5]1=[O:27])([CH3:3])[CH3:2].Cl>CO.[Fe]>[NH2:24][C:22]1[CH:21]=[C:18]([CH:17]=[C:16]([N:6]2[CH2:7][C:8]3[C:9](=[N:10][C:11]([S:14][CH3:15])=[N:12][CH:13]=3)[N:4]([CH:1]([CH3:2])[CH3:3])[C:5]2=[O:27])[CH:23]=1)[C:19]#[N:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 670631623-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)-5-nitrobenzonitrile

Product 1

HCID 670630783-amino-5-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)benzonitrileYield 25.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

3-(1-Isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)-5-nitrobenzonitrile (1.2 g, 3.13 mmol), iron powder (1.75 g, 31 mmol) and conc HCl (0.5 ml, 6 mmol) were combined in methanol (100 mL) by the procedure of Example A10, step 4, to provide 3-amino-5-(1-isopropyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)benzonitrile (280 mg, 25% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.27 (s, 1 H), 6.89 (m, 1 H), 6.86 (d, J=2.0 Hz, 1 H), 6.76 (t, J=2.0 Hz, 1 H), 5.73 (d, J=2.8 Hz, 2 H), 4.98 (m, 1 H), 4.68 (s, 2 H), 2.51 (s, 3 H), 1.48 (d, J=6.8 Hz, 6 H); MS (ESI) m/z: 355.1 [M+H]+.

Sources & evidence

ORD record
ord-584247af519445cb92bb5704bd341579
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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