Sodium Methoxide → HCID 25106205, compound

HRID 1799482Notes

Reaction equation

[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11](Br)=[N:10][N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])[C:8]2=[O:22])=[CH:4][CH:3]=1.[CH3:25][O-:26].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]([O:26][CH3:25])=[N:10][N:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[OH:21])[C:8]2=[O:22])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

According to Scheme 9 Step 2: To a solution of 4-(4-chlorobenzyl)-6-bromo-2-(2-hydroxyphenyl)-1,2,4-triazine-3,5(2H,4H)-dione (0.130 g, 0.32 mmol) in DMF (3 ml) was added, dropwise, at 0° C. a solution 2M of sodium methoxide (0.32 mmol, 0.160 ml). The mixture was stirred 1 h at 0° C. 1 more equivalent of a solution 2M of sodium methoxide was necessary to complete the conversion. Then the reaction mixture was quenched with water. The aqueous layers was neutralised till pH=7 and extracted with ethyl acetate (×3). The organic layer were combined and successively washed with water then, brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 10 g prepacked column, DCM/MeOH 98/2 to afford (30 mg, Yield=26%) 30 mg (Yield=26%) of 4-(4-chlorobenzyl)-2-(2-hydroxyphenyl)-6-methoxy-1,2,4-triazine-3,5(2H,4H)-dione 4.143 were recovered as a white solid.

Workup

customat 0° C.
customThen the reaction mixture was quenched with water
extractionextracted with ethyl acetate (×3)
washsuccessively washed with water
dry with materialbrine, dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography, 10 g

Sources & evidence

ORD record: ord-6308894df785422fa9606dd193971dac
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344138B2

Reaction notes

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