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

HRID 541459Notes

Reaction equation

Br[CH:2]1[CH2:7][O:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]1=O.Cl.[C:12]([C:15]1[C:16]([CH3:26])=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=1)[C:20]([O:22][CH3:23])=[O:21])(=[NH:14])[NH2:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:8][C:4]1([CH3:9])[C:3]2[N:14]=[C:12]([C:15]3[C:16]([CH3:26])=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=3)[C:20]([O:22][CH3:23])=[O:21])[NH:13][C:2]=2[CH2:7][O:6][CH2:5]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-bromo-3,3-dimethyldihydro-2H-pyran-4(3H)-one (compound 449.2, 150 mg, 0.72 mmol), methyl 5-carbamimidoyl-2,4-dimethylbenzoate hydrochloride (compound 2.5, 135 mg, 0.55 mmol), and potassium carbonate (228 mg, 1.65 mmol) in acetonitrile (8 mL) was heated at 100° C. for 48 hrs. The mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (10 mL) and washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (50% ethyl acetate in hexanes) to yield the title compound as a white solid (27 mg, 15%).

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in ethyl acetate (10 mL)
washwashed with brine (20 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-008ae40675e4416d93b8ab7fec8208a9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

Loading…