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

HRID 1484939

反応式

HRID 1484939 の反応式
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]

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 581693555-(5-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-N-tert-butylthiophene-2-sulfonamide

生成物 1

HCID 58169328N-tert-butyl-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-vinylpyrimidin-2-yl)thiophene-2-sulfonamide収率 84.9%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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]+

後処理

  1. temperaturecooled to room temperature
  2. custompartitioned between EtOAc and water
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-6ed90ddae5e54f75ad088b68f89fdc20
出典データセット
uspto-grants-2016_08
特許番号
US09422271B2

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