Lithium hydroxide, monohydrate → HCID 178524764, compound

HRID 1797028Notes

Reaction equation

HRID 1797028 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-9927cbbdc3ea494198370d244d84e72f
Source dataset
uspto-grants-2006_04
Patent number
US07034035B2

Reaction notes

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