Lithium hydroxide, monohydrate → HCID 66729176, compound

HRID 1098601Notes

Reaction equation

HRID 1098601 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 concentrated in vacuo. The crude was dissolved in isopropanol and the solids (LiCl and NaCl) were 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. concentrationconcentrated in vacuo
  8. dissolutionThe crude was dissolved in isopropanol
  9. filtrationthe solids (LiCl and NaCl) were filtered
  10. washwashed with isopropanol
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2eaa42f01eb94f8787d0e4d2153cf81e
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

Loading…