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

HRID 8596

反応式

HRID 8596 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b939b42b0d324149bc288dcb9f098465
出典データセット
uspto-grants-2006_08
特許番号
US07091201B2

関連ノート

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