Dimethylformamide → 2-[(4,6-Dimethoxypyrimidin-2-yl)oxy]naphthalene-1-carbaldehyde

HRID 2050760Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]=[O:13].CN(C)C=O.[H-].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25](S(C)(=O)=O)[N:24]=1>O>[CH3:21][O:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[N:26]=[C:25]([O:1][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]=2[CH:12]=[O:13])[N:24]=1

Participants

Conditions

Temperature: 90 °C

Procedure

8.6 g (0.05 mol) of 2-hydroxynaphthalene-1-aldehyde are introduced into 50 ml of dry dimethylformamide and admixed by stirring, at 0°-5° C., with 1.5 g (0.05 mol) of 80% strength sodium hydride added a little at a time. 10.9 g (0.05 mol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine are then added at room temperature, and the mixture is heated to 90° C. and stirred at that temperature for 6 hours. The solution thus obtained is poured into water. The aqueous mixture is extracted with methylene chloride, carefully washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product is further purified by stirring out with cold toluene, leaving 7.4 g of 2-(4,6-dimethoxypyrimidin-2-yloxy)naphthalene-1-aldehyde of m.p. 123°-125° C.

Workup

additionadded a little at a time
customThe solution thus obtained
extractionThe aqueous mixture is extracted with methylene chloride
washcarefully washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product is further purified
stirringby stirring out with cold toluene

Sources & evidence

ORD record: ord-3e88144aea5c4e848d4f01b26f20ec20
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05015285

Reaction notes

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