Dimethyl methoxymethylenemalonate → Methyl 8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-carboxylate

HRID 1828532Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].C[O:19][CH:20]=[C:21]([C:26](OC)=O)[C:22]([O:24][CH3:25])=[O:23]>C(Cl)Cl>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]3[C:20](=[O:19])[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][N:17]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

4-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-aminopyridine (497 mg) and dimethyl methoxymethylenemalonate (425 mg) were dissolved in methylene chloride, and stirred at 90°0 C. for 2 hours while the solvent was evaporated. The reaction mixture was added with propionic acid (0.5 ml) and heated at 160° C. for 10 hours with stirring. The reaction mixture was cooled, then added with ethyl acetate, washed with saturated sodium hydrogencarbonate and dried over sodium over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the title compound (416 mg).

Workup

customfor 2 hours while the solvent was evaporated
additionThe reaction mixture was added with propionic acid (0.5 ml)
stirringwith stirring
temperatureThe reaction mixture was cooled
additionadded with ethyl acetate
washwashed with saturated sodium hydrogencarbonate
dry with materialdried over sodium over sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9ac72b0c35b0409c988a2d7aac262c1c
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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