Diisopropylethylamine → 2-Thiophen-2-yl-ethanesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide

HRID 8612Notes

Reaction equation

HRID 8612 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[K].[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][CH2:23][S:24]([NH2:27])(=[O:26])=[O:25].CCN(C(C)C)C(C)C>CS(C)=O.O>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:27][S:24]([CH2:23][CH2:22][C:18]2[S:17][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 219795694,6-Dichloro-5-(4-chlorophenyl)-pyrimidineHCID 68897202HCID 68897202, compound

Product 1

HCID 865924732-Thiophen-2-yl-ethanesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amideYield 68.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 4,6-dichloro-5-(4-chlorophenyl)pyrimidine (848 mg), 2-thiophen-2-yl-ethanesulfonic acid amide potassium salt (1.5 g, Referential Example 14) and Hunig's base (1 ml) in DMSO (20 ml) was stirred at rt for 24 h before it was diluted with water (200 ml) and extracted twice with diethyl ether. The aqueous layer was acidified with acetic acid. The precipitate was collected, washed with water and diethyl ether and dried to give 2-thiophen-2-yl-ethanesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide (930 mg) as a beige powder. LC-MS: tR=5.01 min, [M+1]+=413.49, [M−1]−=411.93.

Workup

  1. extractionextracted twice with diethyl ether
  2. customThe precipitate was collected
  3. washwashed with water and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-c9c2f8cbb6934fe4be43d947331b2f89
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Reaction notes

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