Tributylvinyltin → N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide

HRID 1484939

Reaction equation

Br[C:2]1[C:3]([NH:21][C:22]2[CH:26]=[C:25]([CH:27]3[CH2:29][CH2:28]3)[NH:24][N:23]=2)=[N:4][C:5]([C:8]2[S:12][C:11]([S:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])=[O:14])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:30]([Sn](CCCC)(CCCC)C=C)[CH2:31]CC>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].O1CCOCC1>[C:17]([NH:16][S:13]([C:11]1[S:12][C:8]([C:5]2[N:4]=[C:3]([NH:21][C:22]3[CH:26]=[C:25]([CH:27]4[CH2:29][CH2:28]4)[NH:24][N:23]=3)[C:2]([CH:30]=[CH2:31])=[CH:7][N:6]=2)=[CH:9][CH:10]=1)(=[O:15])=[O:14])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 5-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-tert-butylthiophene-2-sulfonamide (1 g, 2.0 mmol, 1.0 eq), tributyl(vinyl)stannane (956 mg, 3.01 mmol, 1.5 eq), Pd (PPh3)2Cl2 (200 mg, 0.28 mmol, 0.14 eq) and Bu4NBr (642 mg, 2.0 mmol, 1.0 eq) in 1,4-dioxane (30 mL) was stirred at 100° C. for 2 h under N2, cooled to room temperature and partitioned between EtOAc and water. The organic layer was concentrated and purified by silica gel chromatography to afford N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide (755 mg, 80%). LC-MS (m/z)=444 [M+H]+

Workup

temperaturecooled to room temperature
custompartitioned between EtOAc and water
concentrationThe organic layer was concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-6ed90ddae5e54f75ad088b68f89fdc20
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Linked notes

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