1,2-Dimethoxyethane → HCID 58942251, compound

HRID 2092338Notes

Reaction equation

HRID 2092338 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([CH3:19])=[C:12](Cl)[C:11]=3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1.[CH3:23][NH:24][C:25]1[N:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30](B3OC(C)(C)C(C)(C)O3)[CH:31]=2)[N:26]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(Cl)Cl.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO.O>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([CH3:19])=[C:12]([C:30]4[CH:31]=[C:32]5[C:27](=[CH:28][CH:29]=4)[N:26]=[C:25]([NH:24][CH3:23])[N:34]=[CH:33]5)[C:11]=3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 16086139N-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)quinazolin-2-amineHCID 58466449HCID 58466449, compound

Product 1

HCID 58942251HCID 58942251, compoundYield 90.3%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 7-(4-methoxybenzyl)-4-chloro-3-methyl-1,7-naphthyridin-8(7H)-one (0.750 g, 2.38 mmol), N-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinazolin-2-amine (0.815 g, 2.86 mmol), dichlorobis(triphenyl-phosphine)palladium (ii) (0.0836 g, 0.119 mmol) and sodium carbonate (0.758 g, 7.15 mmol) was placed in a clear microwave vial along with 10 ml of a combination of 7:3:2 DME:H2O:EtOH. The vial was capped and heated in a Personal Chemistry SmithSynthesizer to 145° C. for 10 minutes. The reaction was diluted with DCM:MeOH (2:1) and the insoluble were filtered off The filtrate was loaded directly on silica gel and purified by column chromatography on silica gel using a gradient of 0 to 10% MeOH in DCM to give 7-(4-methoxybenzyl)-3-methyl-4-(2-(methylamino)quinazolin-6-yl)-1,7-naphthyridin-8(7H)-one (0.940 g, 90.2% yield) as a yellow solid. MS(M+H)− 438.

Workup

  1. customThe vial was capped
  2. filtrationthe insoluble were filtered off The filtrate
  3. custompurified by column chromatography on silica gel using a gradient of 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-f815e261dcc54eeba7678ba50a0063c3
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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