Sodium hydride → 5-(2-ethylbutoxy)-1-(2-ethylbutyl)-3-methylquinazoline-2,4(1H,3H)-dione

HRID 598075Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=[O:13])[NH:8]2.[H-].[Na+].Br[CH2:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22]>CN(C)C=O.O>[CH2:4]([CH:3]([CH2:12][CH3:11])[CH2:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5](=[O:15])[N:6]([CH3:14])[C:7](=[O:13])[N:8]2[CH2:19][CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-methoxy-3-methylquinazoline-2,4(1H,3H)-dione (47 mg, 0.228 mmol) [example 5] in N,N-dimethylformamide (1 ml) was added sodium hydride (8.6 mg, 0.342 mmol). The mixture was stirred at 80° C. for 15 min and 1-bromo-2-ethylbutane (0.064 ml, 0.0753 mmol) was added. The resulting mixture was stirred at 80° C. for 18 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography eluting 50% ethyl acetate/n-hexane to afford 20 mg (32%) of 1-(2-ethylbutyl)-5-hydroxy-3-methyl-2,4(1H,3H)-dione (A) and 9 mg (11%) of 5-(2-ethylbutoxy)-1-(2-ethylbutyl)-3-methylquinazoline-2,4(1H,3H)-dione (B).

Workup

stirringThe resulting mixture was stirred at 80° C. for 18 h
extractionThe aqueous solution was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography
washeluting 50% ethyl acetate/n-hexane

Sources & evidence

ORD record: ord-8b41d791f2e842329fe5f4998601e9d0
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

Loading…