4-Toluenesulfonyl chloride → HCID 12784073, compound

HRID 842060Notes

Reaction equation

HRID 842060 reaction equation
O=[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:3]1.C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:37]([NH2:40])[CH2:38][CH3:39]>CN(C)C=O.O.C(Cl)(Cl)Cl>[C:13]1([C:4]2[N:3]=[C:2]([NH:40][CH2:37][CH2:38][CH3:39])[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7852PropylamineHCID 8471TriethylamineHCID 657593Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate

Product 1

HCID 12784073HCID 12784073, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent3×

Procedure

A mixture of ethyl 3,4-dihydro-4-oxo-2-phenylpyrimidine-5-carboxylate (9.8 g), triethylamine (10.1 g) and dimethylformamide (20 ml) is added dropwise a solution of p-toluenesulfonyl chloride (8.4 g) in dimethylformamide (20 ml) at room temperature, and the mixture is stirred at the same temperature for 10 minutes. To the reaction mixture is added dropwise a solution of propylamine (2.8 g) in dimethylformamide (20 ml), and the mixture is stirred at room temperature for one hour. To the reaction mixture are added chloroform and water, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude ethyl 2-phenyl-4-propylaminopyrimidine-5-carboxylate (11 g).

Workup

  1. stirringthe mixture is stirred at room temperature for one hour
  2. customthe chloroform layer is separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98a1a177db4948f086fb0091a1c82700
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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