Water → Methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate

HRID 604358Notes

Reaction equation

Cl[C:2]1[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:5][C:4]=2[N:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][S:16][C:13]1[N:14]=[CH:15][C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:18]([O:20][CH3:21])=[O:19])=[CH:5][C:4]=3[N:3]=[C:2]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:11]=2[N:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate (1.0 eq, 56 mg, 0.175 mmol) was mixed with benzeneboronic acid (2.0 eq, 43 mg, 0.35 mmol), PdCl2(dppf) (0.1 eq, 13 mg, 0.0178 mmol) and cesium carbonate (2.0 eq, 114 mg, 0.35 mmol) in dioxane (0.5 ml). The mixture was stirred for 10 minutes at 120° C. under microwave heating. Water was added and the resulting precipitate was filtered and dried. After trituration in ethylacetate and hexanes, methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate was isolated by filtration (53 mg, 84% yield). LCMS (ES): >90% pure, m/z 362 [M+1]+.

Workup

temperatureheating
filtrationthe resulting precipitate was filtered
customdried

Sources & evidence

ORD record: ord-7777c8b8edd647be8e5e396c0278ed6d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910600B2

Reaction notes

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