Lithium hydroxide, monohydrate → HCID 66729176, compound

HRID 1930375Notes

Reaction equation

HRID 1930375 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:8]([C:17]([O:19]CC)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.CCO.O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[C:8]([C:17]([OH:19])=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66728977HCID 66728977, compound

Product 1

HCID 66729176HCID 66729176, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a stirring suspension of ethyl 2-tert-butyl-4-morpholinopyrimidine-5-carboxylate (0.36 g, 1.24 mmol) in 1:1:1 THF/EtOH/H2O (9 ml) at RT was added LiOH—H2O (130 mg, 4.95 mmol) and the mixture was stirred overnight at RT. The reaction mixture was checked by LC-MS and the completed reaction was concentrated to an aqueous residue, acidified (pH 3-4) with 3M HCl and the solution was extracted with EtOAc (3×). The combined organics were washed with brine (1×), dried (MgSO4), filtered and concentration. The crude was dissolved in isopropanol and the solid (LiCl and NaCl) was filtered and washed with isopropanol. The filtrate was concentrated to obtain the desired product 2-tert-butyl-4-morpholinopyrimidine-5-carboxylic acid (0.15 g, 46% yield). MS (ESI) m/z: 266.0 (M+H+).

Workup

  1. customthe completed reaction
  2. concentrationwas concentrated to an aqueous residue
  3. extractionthe solution was extracted with EtOAc (3×)
  4. washThe combined organics were washed with brine (1×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentration
  8. dissolutionThe crude was dissolved in isopropanol
  9. filtrationthe solid (LiCl and NaCl) was filtered
  10. washwashed with isopropanol
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-eb62b9c0543a4b68b29b1f96eb0c44aa
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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