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

HRID 533475Notes

Reaction equation

HRID 533475 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.C1C=CC2N(O)N=[N:28]C=2C=1.C(Cl)CCl.[OH-].[NH4+]>CN(C=O)C.O>[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]([NH2:28])=[O:21])=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 580987872-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid

Product 1

HCID 580986642-(Methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(methylthio)-4-(1-phenylcyclopropylamino)pyrimidine-5-carboxylic acid (646 mg, 2.15 mmol) and HOBt.H2O (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-c9632de0541c4898a00df91473e06e90
Source dataset
uspto-grants-2014_10
Patent number
US08853230B2

Reaction notes

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