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

HRID 1983990Notes

Reaction equation

HRID 1983990 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

Procedure

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

Workup

  1. customat about 20° C
  2. concentrationthe reaction medium was concentrated under vacuum almost to dryness
  3. stirringstirred for 20 minutes
  4. filtrationfiltered
  5. washwashed with 3×60 ml of water
  6. dry with materialvacuum dried in the presence of P2O5
  7. customA white solid was obtained

Sources & evidence

ORD record
ord-e95209780a9242838474e9154b87cd26
Source dataset
uspto-grants-2009_06
Patent number
US07544682B2

Reaction notes

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