Ethyl 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylate → 2-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid

HRID 533474Notes

Reaction equation

HRID 533474 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)[C:6]([C:19]([O:21]CC)=[O:20])=[CH:5][N:4]=1>C1COCC1.O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:11][CH2:12]2)[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 58098733Ethyl 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylate

Product 1

HCID 580987872-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylate (crude from step 2) in THF (4 mL) was added LiOHH2O (150 mg, 3.57 mmol) in H2O (2 mL). The mixture was stirred at room temperature overnight. THF was removed under vacuum and the residue was acidified with 1N HCl, white solids precipitated out, which were collected by filtration, dried on vacuum to give 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid (646 mg). MS 302.3 (M+H).

Workup

  1. customTHF was removed under vacuum
  2. customprecipitated out
  3. filtrationwhich were collected by filtration
  4. customdried on vacuum

Sources & evidence

ORD record
ord-be23b1820d3f489a97e26d40e4f451d1
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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