Potassium Carbonate → Methyl 2,4-dimethyl-5-(6-methyl-3,4,6,7-tetrahydropyrano[3,4-d]imidazol-2-yl)benzoate

HRID 541475Notes

Reaction equation

Br[CH:2]1[CH2:7][CH:6]([CH3:8])[O:5][CH2:4][C:3]1=O.BrC1COC(C)CC1=O.Cl.[C:20]([C:23]1[C:24]([CH3:34])=[CH:25][C:26]([CH3:33])=[C:27]([CH:32]=1)[C:28]([O:30][CH3:31])=[O:29])(=[NH:22])[NH2:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:33][C:26]1[CH:25]=[C:24]([CH3:34])[C:23]([C:20]2[NH:21][C:3]3[CH2:4][O:5][CH:6]([CH3:8])[CH2:7][C:2]=3[N:22]=2)=[CH:32][C:27]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

Conditions

Temperature: 75 °C

Procedure

Into around-bottom flask, was placed a mixture of 4-bromo-6-methyldihydro-2H-pyran-3(4H)-one (compound 464.5) and 5-bromo-2-methyldihydro-2H-pyran-4(3H)-one (compound 464.6) (700 mg, 3.63 mmol) as a solution in acetonitrile (20 mL). Methyl 5-carbamimidoyl-2,4-dimethylbenzoate hydrochloride (compound 2.5, 750 mg) and potassium carbonate (1.00 g, 7.25 mmol) were added and the mixture was stirred overnight at 75° C. under nitrogen. The mixture was cooled and the solids were removed by filtration. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:1) as the eluent to obtain the title compound as a yellow solid (100 mg, 9%).

Workup

customInto around-bottom flask, was placed
temperatureThe mixture was cooled
customthe solids were removed by filtration
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:1) as the eluent

Sources & evidence

ORD record: ord-46fbf3561bb646d3b754f262613b652b
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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