4-Chloro-6-(2-methoxyphenyl)pyrimidine → C-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-N-(3-methoxy-propyl)-methanesulfonamide

HRID 1890984Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:19]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])[N:22]=[CH:21][N:20]=1>CN(C=O)C>[CH3:32][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:23]1[N:22]=[CH:21][N:20]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][S:9]([NH:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=2)[CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of C-(3-amino-phenyl)-N-(3-methoxy-propyl)-methanesulfonamide (0.129 g, 0.50 mmol) and 4-chloro-6-(2-methoxyphenyl)-pyrimidine (0.110 g, 0.10 mmol) in DMFA (3 mL) was stirred at 80° C. till the reaction completion (TLC control), then evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel yielding C-{3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-N-(3-methoxy-propyl)-methanesulfonamide

Workup

customevaporated in vacuo
customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-6b7cb39ae9a04729be4695fc76840799
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507498B2

Reaction notes

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