Diisopropylethylamine → 2-Phenyl-ethanesulfonic acid (6-chloro-2-pyridin-4-yl-5-p-tolyl-pyrimidin-4-yl)-amide

HRID 8596

Reaction equation

HRID 8596 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:3]=1.[K].[C:23]1([CH2:29][CH2:30][S:31]([NH2:34])(=[O:33])=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>CS(C)=O.O>[Cl:15][C:6]1[N:5]=[C:4]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[N:3]=[C:2]([NH:34][S:31]([CH2:30][CH2:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:32])=[O:33])[C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 219795754,6-Dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidineHCID 688981502-Phenyl-ethanesulfonic acid amide potassium salt

Product 1

HCID 865924702-Phenyl-ethanesulfonic acid (6-chloro-2-pyridin-4-yl-5-p-tolyl-pyrimidin-4-yl)-amideYield 21.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 4,6-dichloro-2-(4-pyridyl)-5-(p-tolyl)-pyrimidine (1.5 g), 2-phenyl-ethanesulfonic acid amide potassium salt (1.44 g, Referential Example 1e) and Hunig's base (1 ml) in DMSO (20 ml) was stirred at rt for 24 h before it was diluted with water (150 ml) and extracted twice with diethyl ether. The aqueous layer was acidified with acetic acid. The precipitate was collected, and further purified by column chromatography on silica gel eluting with hexane:EA 1:1 to give 2-phenyl-ethanesulfonic acid (6-chloro-2-pyridin-4-yl-5-p-tolyl-pyrimidin-4-yl)-amide (480 mg) as a foam. LC-MS: tR=5.08 min, [M+1]+=465.13, [M−1]−=462.96.

Workup

  1. extractionextracted twice with diethyl ether
  2. customThe precipitate was collected
  3. customfurther purified by column chromatography on silica gel eluting with hexane:EA 1:1

Sources & evidence

ORD record
ord-b939b42b0d324149bc288dcb9f098465
Source dataset
uspto-grants-2006_08
Patent number
US07091201B2

Linked notes

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