1,2-Dichloroethane → 2-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxamide

HRID 384271Notes

Reaction equation

HRID 384271 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]([OH:21])=O)=[CH:5][N:4]=1.C(Cl)CCl.[OH-].[NH4+:27].O>CN(C=O)C>[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]([NH2:27])=[O:21])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 962WaterHCID 14923Ammonium HydroxideHCID 580987872-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 580986642-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid (646 mg, 2.15 mmol) and HOBtH2O (395 mg, 2.58 mmol) in DMF (3.5 mL), EDC (515 mg, 2.69 mmol) was added. The mixture was stirred at room temperature for 20 min. Ammonium hydroxide (244 mg, 4.30 mmol) was added. It was stirred at room temperature for 1 h. Water was added to induce precipitation, the solids were collected by filtration to give 2-(methylthio)-4-(1-phenylcyclopropylamino) pyrimidine-5-carboxamide (636 mg). MS 301.2 (M+H).

Workup

  1. stirringIt was stirred at room temperature for 1 h
  2. customprecipitation
  3. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-81a0cb4fef2a4c7c891837c3780532dd
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

Loading…