Ammonium Hydroxide → 5-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl ester

HRID 1784523Notes

Reaction equation

HRID 1784523 reaction equation
[NH4+:1].[OH-].Cl[C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1>CCO>[NH2:1][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 2226665-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

140 ml of a 20% NH4OH solution are added, in 20 minutes, and while maintaining the temperature at around 20° C., to a suspension of 50.7 g of ethyl 4-chloro-2-(methylthio)pyrimidin-5-carboxylate in 400 ml of EtOH. After stirring at ambient temperature for 20 hours, the reaction medium is concentrated under vacuum almost to dryness, and the residue is then taken up in 350 ml of water, stirred for 20 minutes, filtered, washed with 3×60 ml of water, and then dried under vacuum in the presence of P2O5. A white solid is obtained, Mp=134-135° C., m=39.9 g.

Workup

  1. concentrationthe reaction medium is concentrated under vacuum almost to dryness
  2. stirringstirred for 20 minutes
  3. filtrationfiltered
  4. washwashed with 3×60 ml of water
  5. dry with materialdried under vacuum in the presence of P2O5
  6. customA white solid is obtained

Sources & evidence

ORD record
ord-900acc20278b45259bc9294c07deb951
Source dataset
uspto-grants-2009_03
Patent number
US07504406B2

Reaction notes

Loading…