Triethylamine → 5-Bromo-2-(methylsulfanyl)-4-[(methylsulfonyl)methyl]pyrimidine

HRID 531226ノート

反応式

HRID 531226 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[C:8]([CH2:15]O)=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1.CCN(CC)CC>C(Cl)Cl>[Br:6][C:7]1[C:8]([CH2:15][S:2]([CH3:1])(=[O:4])=[O:3])=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66524860(5-Bromo-2-(methylthio)pyrimidin-4-yl)methanol2 回

生成物 1

HCID 772307075-Bromo-2-(methylsulfanyl)-4-[(methylsulfonyl)methyl]pyrimidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Methanesulfonyl chloride (5.85 g, 51.0 mmol) was added to a stirred, cooled 0° C. mixture of [5-bromo-2-(methylthio)pyrimidin-4-yl]methanol (INTERMEDIATE 1, 10 g, 42.5 mmol) in CH2Cl2 (200 mL), followed by addition of Et3N (6.46 g, 63.8 mmol). The mixture was stirred at 0° C. for 30 minutes. TLC showed no starting material left. The mixture was quenched with water (30 mL) and the mixture was washed with more water (50 mL). The organic portion was washed with brine (saturated, 50 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography, eluting with EtOAc/hexane (3/7) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 8.61 (s, 1H), 5.38 (s, 2H), 3.21 (s, 3H), 2.60 (s, 3H).

後処理

  1. waitleft
  2. customThe mixture was quenched with water (30 mL)
  3. washthe mixture was washed with more water (50 mL)
  4. washThe organic portion was washed with brine (saturated, 50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluting with EtOAc/hexane (3/7)

出典と根拠

ORDレコード
ord-9523fc0df1404210b9ebefe97b8a30bf
出典データセット
uspto-grants-2016_05
特許番号
US09353101B2

反応ノート

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