HCID 18452873, compound → Formate
Reaction equation
C([O:5][C:6]([C:8]1[N:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])(C)(C)C>C(O)=O>[N:9]1[CH:10]=[CH:11][CH:12]=[N:13][C:8]=1[C:6]([OH:7])=[O:5].[CH:6]([O-:7])=[O:5]Participants
4
Reactant 1
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
The carboxylic t-butyl ester was dissolved in one hundred times an equal volume of 96% formic acid, and the solution was heated to 70° C. for 2 h. At this time, TLC of an evaporated aliquot of the reaction mixture indicated complete conversion of the pyrimidine-carboxylic t-butyl ester. The formic acid was removed by rotary evaporation under high vacuum to afford the pyrimidine-carboxylic acid as a formate salt. Typically, the obtained product was >98% pure, but if necessary, the product was purified by preparative reverse-phase HPLC, or by flash chromatography on silica gel using EtOAc/hexanes, or by recrystallization.
Workup
- customThe formic acid was removed by rotary evaporation under high vacuum
Sources & evidence
- ORD record
- ord-6d6c9d69b794458c8d6991314514bef7
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07205310B2
Reaction notes
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