Sodium Hydroxide → (Pyrimidin-4-yl)acetic acid

HRID 1483981Notes

Reaction equation

HRID 1483981 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10]CC)=[O:9])=[N:3][CH:2]=1.[OH-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20295406Ethyl 2-(pyrimidin-4-yl)acetate

Product 1

HCID 21486925(Pyrimidin-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(pyrimidin-4-yl)acetate (Example 33b, 450 mg, 2.71 mmol) in ethanol (5 mL) was added 2N NaOH (2 mL) at room temperature under nitrogen. The reaction mixture was stirred at room temperature under nitrogen for 24 hours, concentrated under reduced pressure and suspended in ethanol. The solid was removed by vacuum filtration, and the filtrate was concentrated under reduced pressure, triturated with ethanol, concentrated again and carried onto the next step without further purification. MS 139 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe solid was removed by vacuum filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customtriturated with ethanol
  5. concentrationconcentrated again
  6. customcarried onto the next step without further purification

Sources & evidence

ORD record
ord-361ede2119cf4039907e1de3ac2f6a9d
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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