(3-Aminophenyl)methanesulfonamide → (3-{6-[2-(Tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidin-4-ylamino}-phenyl)-methanesulfonamide

HRID 1891009Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH2:27][CH:28]2[CH2:32][CH2:31][CH2:30][O:29]2)[N:17]=[CH:16][N:15]=1>CN(C=O)C>[O:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[CH2:27][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:18]1[N:17]=[CH:16][N:15]=[C:14]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][S:9]([NH2:12])(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=2)[CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of (3-amino-phenyl)-methanesulfonamide (0.18 g, 0.62 mmol) and 4-chloro-6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidine (0.115 g, 0.62 mmol) in DMF (3 mL) was stirred at 80-90° C. till the reaction completion (TLC control), then evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel yielding (3-{6-[2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-pyrimidin-4-ylamino}-phenyl)-methanesulfonamide (Compound 82) as white solid.

Workup

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

Sources & evidence

ORD record: ord-ecadf2fd796146ed823dbc01d51eb61c
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507498B2

Reaction notes

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