6-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione → 3-(6-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

HRID 60459

Reaktionsgleichung

[Br:1][C:2]1[CH:24]=[N:23][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[N:8]([CH2:11][CH2:12][CH2:13][O:14][CH:15]3CCCC[O:16]3)[C:9](=[O:10])[C:4]=2[C:3]=1[CH:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)O>C(O)=O.[Zn]>[CH:15]([O:14][CH2:13][CH2:12][CH2:11][N:8]1[C:9](=[O:10])[C:4]2[C:3]([CH2:25][C:27]3[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=3)=[C:2]([Br:1])[CH:24]=[N:23][C:5]=2[N:6]([CH3:22])[C:7]1=[O:21])=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 6-bromo-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (800 mg, 1.50 mmol) in HCOOH (10 mL) was added Zn dust (484 mg, 7.50 mmol). The reaction was heated at 60° C. for 2 h cooled to RT and filtered. The filtrate was concentrated to give 3-(6-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (70 mg, 10% yield) as an oil. LCMS: MH+ 466 and TR=1.753 min. Used without further purification.

Aufarbeitung

temperaturecooled to RT
filtrationfiltered
concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag: ord-936ce9997ba7433984e41318f5bcb48b
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09440972B2

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