Lithium hydroxide, monohydrate → HCID 178524764, compound
Reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[CH:4][N:3]=1.O[Li].O>C1COCC1.CO>[OH:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[CH:4][N:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Ethyl 4-hydroxypyrimidine-5-carboxylate can be prepared following the procedure of M. Pesson et al., Eur. J. Med. Chem.—Chim. Ther. 1974, 9, 585. A solution of this ester (500 mg, 3 mmol) in THF (10 mL) and MeOH (5 mL) was treated with LiOH.H2O (373 mg, 8.9 mmol) and stirred overnight. The mixture was quenched with conc. HCl (1 mL) and extracted with EtOAc (2×20 mL). The combined organic extract was dried (MgSO4) and concentrated to give 260 mg of the title compound 19 as an orange solid, m.p. 220° C. (dec). 4-HYDROXY-2-METHYLPYRIMIDINE-5-CARBOXYLIC ACID (20).
Workup
- customThe mixture was quenched with conc. HCl (1 mL)
- extractionextracted with EtOAc (2×20 mL)
- extractionThe combined organic extract
- dry with materialwas dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-090e5247b0a549bb915a20b3649cda76
- Source dataset
- uspto-grants-2008_01
- Patent number
- USRE039991E1
Reaction notes
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