Lithium hydroxide, monohydrate → 2-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid

HRID 384270Notes

Reaction equation

HRID 384270 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.O[Li].O>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

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 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 LiOH.H2O (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-469f60f002e24906ace889bfbaca4df7
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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