Lithium Hydroxide → HCID 18375083, compound

HRID 2407697Notes

Reaction equation

HRID 2407697 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([C:16]([O:18]CC)=[O:17])=[CH:5][N:4]=1.[OH-].[Li+]>C(O)C>[NH:9]([C:7]1[C:6]([C:16]([OH:18])=[O:17])=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 295672Ethyl 2-(methylthio)-4-(phenylamino)pyrimidine-5-carboxylate

Product 1

HCID 18375083HCID 18375083, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(methylthio)-4-(phenylamino)pyrimidine-5-carboxylate (4.0 g, prepared according to the reported preparation in Barvian, M.; et al. J. Med. Chem. 2000, 43, 4606) in ethanol (50 mL) was treated with 2 N lithium hydroxide (50 mL) at room temperature for 16 hours. The reaction mixture was washed with ether and then brought to pH 6 via the addition of 1 N hydrochloric acid. The resulting precipitate was collected by filtration, azeotroped with toluene and dried under vacuum to obtain the title compound (2.2 g) having the following physical data.

Workup

  1. customaccording to the reported preparation in Barvian, M
  2. washThe reaction mixture was washed with ether
  3. additionbrought to pH 6 via the addition of 1 N hydrochloric acid
  4. filtrationThe resulting precipitate was collected by filtration
  5. customazeotroped with toluene
  6. customdried under vacuum

Sources & evidence

ORD record
ord-203e2b7f8663480e9c63d75165a276fa
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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