Sodium Chloride → HCID 67513398、化合物

HRID 705031

反応式

HRID 705031 の反応式
Br[C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[C:21]([Si:23]([CH3:26])([CH3:25])[CH3:24])#[CH:22].[Cl-].[Na+]>O1CCCC1.[Cu]I.Cl[Pd](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][Si:23]([C:21]#[C:22][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=1)([CH3:26])[CH3:25]

参加物

8

反応物 4

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 158812582-(6-Bromopyridin-2-yl)pyrimidine

生成物 1

HCID 67513398HCID 67513398、化合物

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178479802HCID 178479802、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

1.00 g (3.99 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine, 45.5 mg (239 μmol) of copper(I) iodide and 670 μl (4.78 mmol) of N-isopropylpropane-2-amine were initially charged in 15 ml of tetrahydrofuran and degassed in an ultrasonic bath under argon. The reaction mixture was then heated to 50° C., 168 mg (239 mol) of dichloro[bis(triphenylphosphoranyl)]palladium were added and 1.70 ml (12.0 mmol) of ethynyl(trimethyl)silane were added dropwise over a period of one hour. The mixture was then stirred at 60° C. for a further two hours. For work-up, the mixture was added to semiconcentrated sodium chloride solution, the mixture was filtered through Celite and the aqueous phase was extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, concentrated and purified chromatographically. This gave 520 mg (51% of theory) of 2-{6-[(trimethylsilyl)ethynyl]pyridin-2-yl}pyrimidine.

後処理

  1. customdegassed in an ultrasonic bath under argon
  2. filtrationthe mixture was filtered through Celite
  3. extractionthe aqueous phase was extracted repeatedly with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified chromatographically

出典と根拠

ORDレコード
ord-1298a6f452cc400ca0b63f7166fb57a9
出典データセット
uspto-grants-2015_11
特許番号
US09173396B2

関連ノート

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