Citric Acid → 2-Thiophen-2-yl-ethanesulfonic acid [5-(4-chloro-phenyl)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-amide

HRID 8613Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([CH2:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)(=[O:11])=[O:10])[C:3]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.C(O)(=O)C[C:28](CC(O)=O)([C:30](O)=[O:31])[OH:29]>C(O)CO.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:3]2[C:4]([NH:8][S:9]([CH2:12][CH2:13][C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)(=[O:11])=[O:10])=[N:5][CH:6]=[N:7][C:2]=2[O:29][CH2:28][CH2:30][OH:31])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 110 °C

Procedure

2-Thiophen-2-yl-ethanesulfonic acid [6-chloro-5-(4-chloro-phenyl)-pyrimidin-4-yl]-amide (930 mg) was added to a solution of K-tert. butylate (1.16 g) in ethylene glycol (10 ml). The mixture was stirred at 110° C. for 12 h before it was diluted with water (150 ml), acidified with 10% aq. citric acid (13 ml). The resulting precipitate was collected, washed with water and diethyl ether and dried to give (820 mg) 2-thiophen-2-yl-ethanesulfonic acid [5-(4-chloro-phenyl)-6-(2-hydroxy-ethoxy) -pyrimidin-4-yl]-amide as a beige powder. LC-MS: tR=4.43 min, [M+1]+=440.01, [M−1]−=437.99.

Workup

customThe resulting precipitate was collected
washwashed with water and diethyl ether
customdried

Sources & evidence

ORD record: ord-8a743ff8858e40c99c6d6143fe72b8cd
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091201B2

Reaction notes

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