1,2-Dimethoxyethane → Ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2]bipyrimidinyl-4-yl]-amide

HRID 2252728Notes

Reaction equation

CC(C)([O-])C.[K+].C[O:8][CH2:9][CH2:10][O:11]C.Cl[C:14]1[N:19]=[C:18]([C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:17]=[C:16]([NH:26][S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[C:15]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40]>C(O)CO>[OH:8][CH2:9][CH2:10][O:11][C:14]1[N:19]=[C:18]([C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:17]=[C:16]([NH:26][S:27]([CH2:30][CH3:31])(=[O:29])=[O:28])[C:15]=1[O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of potassium tert.-butoxide (366.5 mg) in ethylene glycol (5 ml) was added 1,2-dimethoxy ethane (5 ml) and ethanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl-4-yl]-amide (420 mg). The reaction mixture was heated to 85° C. for 7 days, concentrated in vacuo, poured onto water, acidified by 2N HCl, and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo. The precipitated product was washed with diethyl ether, filtered and dried at HV to give ethanesulfonic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl-4-yl]-amide (400 mg). LC-MS: tR: 3.45, [M+H]+: 448.24.

Workup

concentrationconcentrated in vacuo
additionpoured onto water
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried over magnesium sulfate
concentrationconcentrated in vacuo
washThe precipitated product was washed with diethyl ether
filtrationfiltered
customdried at HV

Sources & evidence

ORD record: ord-daca05c35a284770ab324c5d6ee82d46
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323465B2

Reaction notes

Loading…