Sodium Hydroxide → HCID 67997085, compound

HRID 45787Notes

Reaction equation

HRID 45787 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:18]([S:19][CH2:20][C:21]([O:23]C)=[O:22])=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]2[C:18]([S:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67997035HCID 67997035, compound

Product 1

HCID 67997085HCID 67997085, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-(4-(4-cyanonaphthalen-1-yl)pyrimidin-5-ylthio)acetate (22 mg, 0.065 mmol), aqueous sodium hydroxide solution (1M, 0.5 mL) and methanol (1 mL) was stirred at room temperature for 2 hours. Methanol was removed and aqueous sodium hydroxide solution (1M, 1 mL) and ethyl acetate (3 mL) were added. The aqueous layer was removed, acidified and extracted with ethyl acetate. The second organic layer was concentrated to dryness to yield 2-(4-(4-cyanonaphthalen-1-yl)pyrimidin-5-ylthio)acetic acid (19 mg, 91%).

Workup

  1. customMethanol was removed
  2. additionaqueous sodium hydroxide solution (1M, 1 mL) and ethyl acetate (3 mL) were added
  3. customThe aqueous layer was removed
  4. extractionextracted with ethyl acetate
  5. concentrationThe second organic layer was concentrated to dryness

Sources & evidence

ORD record
ord-81fe4a4e16fd461bb15e57e4d0e9c36c
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

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