Citric Acid → n-Propanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide

HRID 2252725Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])[C:6]=1[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.[H-].[Na+].Cl[C:28]1[N:33]=[CH:32][C:31]([Br:34])=[CH:30][N:29]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Br:34][C:31]1[CH:30]=[N:29][C:28]([O:1][CH2:2][CH2:3][O:4][C:5]2[N:10]=[CH:9][N:8]=[C:7]([NH:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:13])=[O:14])[C:6]=2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[N:33][CH:32]=1

Participants

Conditions

Temperature: 50 °C

Procedure

n-Propanesulfonic acid [6-(2-hydroxy-ethoxy)-5-p-tolyl-pyrimidin-4-yl]-amide (115 mg) was dissolved in THF (15 ml). Sodium hydride (60 mg) was added followed by stirring for 15 min at 50° C. Then 2-chloro-5-bromo-pyrimidine (135 mg) was added and stirring was continued for 8 h at 75° C. The reaction mixture was poured onto ice water, acidified with solid citric acid and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and the solvent was evaporated. The crude material was purified by plate chromatography with diethyl ether to give n-propanesulfonic acid {6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-p-tolyl-pyrimidin-4-yl}-amide (65 mg) as a white powder. LC-MS: tR: 4.91, [M+H]+: 510.13.

Workup

stirringstirring
waitwas continued for 8 h at 75° C
additionThe reaction mixture was poured onto ice water
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
customthe solvent was evaporated
customThe crude material was purified by plate chromatography with diethyl ether

Sources & evidence

ORD record: ord-69cf8aa40f0c4fabb34d81ee0b441875
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323465B2

Reaction notes

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