Ethylenediamine → 1-Methyl-3-(2-methyl-4-nitrophenyl)tetrahydropyrimidin-2(1H)-one

HRID 218524Notes

Reaction equation

P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[CH3:19].[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][NH:23][C:22]1=[O:27].NCCN>O1CCOCC1.[Cu]I>[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[CH3:19])[C:22]1=[O:27]

Participants

Conditions

Temperature: 110 °C

Procedure

16.1 g (76.1 mmol) of potassium phosphate and 0.362 g (1.90 mmol) of copper(I) iodide are initially charged, and the apparatus is baked out and then flushed with argon. 10.0 g (38.1 mmol) of 1-iodo-2-methyl-4-nitrobenzene, 6.51 g (57.0 mmol) of 1-methyltetrahydropyrimidin-2(1H)-one and 0.394 g (3.80 mmol) of N,N′-dimethylenediamine in 200 ml of dioxane are added, and the mixture is stirred at 110° C. After 19 h, after cooling, the mixture is filtered with suction through kieselguhr and then washed three times with 100 ml of ethyl acetate. The solvent is removed under reduced pressure and the residue is purified by chromatography on silica gel (2:1→1:1 cyclohexane/ethyl acetate). This affords 5.94 g (63% of theory) of the desired compound.

Workup

customflushed with argon
temperatureafter cooling
filtrationthe mixture is filtered with suction through kieselguhr
washwashed three times with 100 ml of ethyl acetate
customThe solvent is removed under reduced pressure
customthe residue is purified by chromatography on silica gel (2:1→1:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-ba33e8432fa84103a431bb4b22c92229
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198267B2

Reaction notes

Loading…