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

HRID 1828507Notes

Reaction equation

[OH:1][C:2]1[N:3]=[C:4]2[CH:16]=[C:15]([CH2:17][CH2:18][C:19]3[S:20][CH:21]=[C:22]([CH:24]([CH3:26])[CH3:25])[N:23]=3)[CH:14]=[CH:13][N:5]2[C:6](=[O:12])[C:7]=1/[CH:8]=[CH:9]/[C:10]#[N:11].CN(C)C=O.C(N(C(C)C)CC)(C)C.I[CH2:42][CH:43]1[CH2:47][CH2:46][O:45][CH2:44]1>O.C(Cl)(Cl)Cl>[CH:24]([C:22]1[N:23]=[C:19]([CH2:18][CH2:17][C:15]2[CH:14]=[CH:13][N:5]3[C:6](=[O:12])[C:7](/[CH:8]=[CH:9]/[C:10]#[N:11])=[C:2]([O:1][CH2:42][CH:43]4[CH2:47][CH2:46][O:45][CH2:44]4)[N:3]=[C:4]3[CH:16]=2)[S:20][CH:21]=1)([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

(E)-2-{2-Hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido-[1,2-a]pyrimidin-3-yl}-1-ethenylcyanide (100 mg) was added with dimethylformamide (5 ml), diisopropylethylamine (500 ml) and 3-(iodomethyl)tetrahydrofuran (200 ml), and then the mixture was stirred at 80° C. for 2 hours and further stirred overnight at room temperature. After the reaction mixture was distributed between chloroform and water, the organic layer was 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 (51 mg).

Workup

stirringfurther stirred overnight at room temperature
dry with materialthe organic layer was dried 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-2310b9414fe84d4495c05f6cc50a8793
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

Loading…