Lithium hydroxide, monohydrate → HCID 66958350, compound

HRID 1912651Notes

Reaction equation

HRID 1912651 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+]>CO>[CH2:1]([O:8][C:9]1[C:10]([C:22]([OH:24])=[O:23])=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66958428HCID 66958428, compound

Product 1

HCID 66958350HCID 66958350, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of benzyl 5-(benzyloxy)-6-p-tolylpyrimidine-4-carboxylate P71 (90 mg, 0.22 mmol) in methanol (5 mL) was added lithium hydroxide monohydrate (46 mg, 1.10 mmol). The reaction mixture was heated in a microwave reactor at 90° C. for 10 minutes. The organic solvent was evaporated under reduced pressure. Ethyl acetate and 1 N hydrochloric acid were added. The organic layer was washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure. The solid product was dried under reduced pressure to afford the desired 5-(benzyloxy)-6-p-tolylpyrimidine-4-carboxylic acid P72 (70 mg, 0.22 mmol).

Workup

  1. customThe organic solvent was evaporated under reduced pressure
  2. additionEthyl acetate and 1 N hydrochloric acid were added
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure
  6. customThe solid product was dried under reduced pressure

Sources & evidence

ORD record
ord-09a3cfa3d91f488aaafcdda49629cebe
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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