Cesium carbonate → Methylenedioxyphenoxy-pyrimidine

HRID 1582939Notes

Reaction equation

HRID 1582939 reaction equation
Cl[C:2]1[C:7](C(OCC)=O)=[CH:6][N:5]=[CH:4][N:3]=1.C1O[C:20]2[CH:19]=[CH:18][C:17]([OH:22])=[CH:16][C:15]=2O1.[C:23](=O)([O-:25])[O-:24].[Cs+].[Cs+].[H-].[Na+]>CN(C)C=O>[CH2:23]1[O:25][C:7]2[C:2](=[N:3][C:4]([O:22][C:17]3[CH:18]=[CH:19][CH:20]=[CH:15][CH:16]=3)=[N:5][CH:6]=2)[O:24]1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 24758Sodium hydrideHCID 68289SesamolHCID 12684326Ethyl 4-chloropyrimidine-5-carboxylate

Product 1

HCID 69840746Methylenedioxyphenoxy-pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In reaction 1 of Scheme (10.2.0) the 4-chloro-5-carboethoxy-pyrimidine of Formula (3.0.0) in anhydrous dimethylformamide (DMF) is reacted with 3,4-methylenedioxyphenol of Formula (3.0.1) in the presence of cesium carbonate, or sodium hydride, to form the methylenedioxyphenoxy-pyrimidine of Formula (3.0.2). The reaction mixture comprising (3.0.0) and (3.0.1) is heated to a temperature of from 80° to 100° C., preferably 90° C., for a time period of from 1 hour to 24 hours, preferably 18 hours.

Sources & evidence

ORD record
ord-1159dfbe9852475ab15b09ba5f070040
Source dataset
uspto-grants-2004_05
Patent number
US06740655B2

Reaction notes

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