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

HRID 8593

Reaction equation

[K].[C:2]1([CH2:8][CH2:9][S:10]([NH2:13])(=[O:12])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:20]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[C:19](Cl)[N:18]=[CH:17][N:16]=1.CCN(C(C)C)C(C)C>CS(C)=O.O>[Cl:14][C:15]1[N:16]=[CH:17][N:18]=[C:19]([NH:13][S:10]([CH2:9][CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:11])=[O:12])[C:20]=1[C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 2-phenyl-ethanesulfonic acid amide potassium salt (3.0 g), 4,6-dichloro-5-p-tolyl-pyrimidine (2.15 g) and Hunig's base (1.57 ml) in DMSO (50 ml) was stirred at rt for 20 h before it was diluted with water (500 ml) and extracted twice with diethyl ether (250 ml). The aqueous phase was acidified with acetic acid. The resulting suspension was cooled to 5° C. and filtered. The solid material was washed with water and diethyl ether, and dried at 40° C. under high vacuum to give 2-phenyl-ethanesulfonic acid (6-chloro-5-p-tolyl-pyrimidin-4-yl)-amide (2.08 g) as a grey powder. LC-MS: tR=5.23 min, [M+1]+=388.18, [M−1]−=386.14.

Workup

extractionextracted twice with diethyl ether (250 ml)
filtrationfiltered
washThe solid material was washed with water and diethyl ether
customdried at 40° C. under high vacuum

Sources & evidence

ORD record: ord-de2c64610930487e978e7f18ba39fabb
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091201B2

Linked notes

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