Water → 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid

HRID 1470304Notes

Reaction equation

HRID 1470304 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17]CC2C=CC=CC=2)=[O:16])=[CH:13][N:12]=[C:11]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O.[OH-].[K+]>CCO>[CH2:1]([O:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[CH:13][N:12]=[C:11]([N:25]2[CH:29]=[CH:28][CH:27]=[N:26]2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 67459462Benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate

Product 1

HCID 674594834-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acidYield 13%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of benzyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate, 2-d, (2 g crude) in EtOH(20 ml)/THF (20 ml)/water (20 ml) was added KOH (0.87 g, 15.5 mmol). The mixture was stirred at room temperature for 12 hours. The mixture was then concentrated under vacuum and the residue was diluted with water and basified to pH=2 with HCl followed by extraction with ethyl acetate. The organic layer was brine washed, dried over sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column with the eluent of petroleum ether/ethyl acetate=7/1 to afford the compound 2-e (200 mg, 13%).

Workup

  1. concentrationThe mixture was then concentrated under vacuum
  2. additionthe residue was diluted with water and basified to pH=2 with HCl
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashed
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica gel column with the eluent of petroleum ether/ethyl acetate=7/1

Sources & evidence

ORD record
ord-ac54a65de9b4495aa376192c53b5c98a
Source dataset
uspto-grants-2015_04
Patent number
US09006433B2

Reaction notes

Loading…