Dimethylformamide → tert-Butyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-2-(tetrahydro-3-furanylmethoxy)-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoate

HRID 1828505Notes

Reaction equation

[OH:1][C:2]1[N:3]=[C:4]2[CH:21]=[C:20]([CH2:22][CH2:23][C:24]3[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=3)[CH:19]=[CH:18][N:5]2[C:6](=[O:17])[C:7]=1/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].CN(C)C=O.C(N(C(C)C)CC)(C)C.I[CH2:47][CH:48]1[CH2:52][CH2:51][O:50][CH2:49]1>[Cl-].[Na+].O.C(OCC)(=O)C>[CH:29]([C:27]1[N:28]=[C:24]([CH2:23][CH2:22][C:20]2[CH:19]=[CH:18][N:5]3[C:6](=[O:17])[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])=[C:2]([O:1][CH2:47][CH:48]4[CH2:52][CH2:51][O:50][CH2:49]4)[N:3]=[C:4]3[CH:21]=2)[S:25][CH:26]=1)([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl (E)-3-(2-hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl)-2-propenoate (17 mg) was added with dimethylformamide (3 ml), diisopropylethylamine (500 ml) and 3-(iodomethyl)tetrahydrofuran (50 ml), and then the mixture was stirred at 80° C. for 16 hours. The reaction mixture was added with ethyl acetate and saturated brine, and the organic layer was further washed twice with saturated brine and dried over magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography to obtain the title compound (14 mg).

Workup

washthe organic layer was further washed twice with saturated brine
dry with materialdried over magnesium sulfate
customAfter the solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-ca10dc81d3c4423d8d8932559e3f46e0
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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