Lithium hydroxide, monohydrate → HCID 178524764, compound

HRID 2249336Notes

Reaction equation

HRID 2249336 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]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178469817HCID 178469817, compound

Product 1

HCID 178524764HCID 178524764, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

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

  1. customThe mixture was quenched with conc. HCl (1 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-090e5247b0a549bb915a20b3649cda76
Source dataset
uspto-grants-2008_01
Patent number
USRE039991E1

Reaction notes

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