Methyl 4-methyl-3-oxopentanoate → 1-(2-(2,6-dimethylphenyl)-4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione

HRID 80765

Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([O:19][CH3:20])[C:12]2[CH2:18][NH:17][CH2:16][CH2:15][C:13]=2[N:14]=1.[CH3:21][CH:22]([CH3:30])[C:23](=[O:29])[CH2:24][C:25](OC)=[O:26]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]1[N:10]=[C:11]([O:19][CH3:20])[C:12]2[CH2:18][N:17]([C:25](=[O:26])[CH2:24][C:23](=[O:29])[CH:22]([CH3:30])[CH3:21])[CH2:16][CH2:15][C:13]=2[N:14]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of 2-(2,6-dimethylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (4.8 g, 17.82 mmol), methyl 4-methyl-3-oxopentanoate (5.14 g, 35.6 mmol), and DMAP (0.327 g, 2.67 mmol) was dissolved in toluene (70 mL). The mixture was evenly divided into four 20 mL microwave vials. Each vial was heated to 150° C. for 30 min via microwave irradiation. The reaction mixtures were combine and directly concentrated. The resulting residue was purified via silica gel FCC (0-80% EtOAc/heptane) to give 1-(2-(2,6-dimethylphenyl)-4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione. MS (ESI+) m/z 382.3 (M+H)+.

Aufarbeitung

customThe reaction mixtures
concentrationdirectly concentrated
customThe resulting residue was purified via silica gel FCC (0-80% EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag: ord-2d40f3e3235141af880e9afa258ab03e
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846656B2

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