Water → HCID 53877421, compound

HRID 1003156Notes

Reaction equation

I[C:2]1[C:3](=[O:17])[N:4]([C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5][O:6][C:7]=1[CH3:8].C([Sn](CCCC)(CCCC)[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)CCC.[Cl-].[Li+].O>O1CCCC1>[CH3:8][C:7]1[O:6][CH2:5][N:4]([C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3](=[O:17])[C:2]=1[C:23]1[S:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of ethyl 2-(2,3-dihydro-5-iodo-6-methyl-4-oxo-4H-1,3-oxazin-3-yl)-2-methylpropanoate (30.0 g), 2-(tributylstannyl)thiophene (33.5 ml), palladium bis-triphenylphosphine chloride (3.08 g) and lithium chloride (20.5 g) in tetrahydrofuran was heated at 50° C. for 24 hours. Further 2-(tributylstannyl)thiophene (2.8 ml) was added and the mixture heated for a further 18 hours. Palladium bis-triphenylphosphine chloride (0.62 g) was added and heating continued for 18 hours. The mixture was poured into water, extracted (ether) and the organic phase washed (brine), dried (magnesium sulphate) and evaporated. Purification by chromatography on silica gel gave ethyl [2,3-dihydro-6-methyl-4-oxo-5-(2-thienyl)-4H-1,3-oxazine-3-yl]-2-methylpropanoate (14.5 g), NMR 1.15(t,3H), 1.55(s,6H), 2.1(s,3H), 4.15(q,2H), 5.25(s,2H), 6.9-7.4(m,3H).

Workup

temperaturethe mixture heated for a further 18 hours
temperatureheating
extractionextracted (ether)
washthe organic phase washed (brine)
dry with materialdried (magnesium sulphate)
customevaporated
customPurification by chromatography on silica gel

Sources & evidence

ORD record: ord-d9d70fdc36764600989484f075d673dc
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046135

Reaction notes

Loading…