Sodium Chloride → HCID 67513398, 화합물

HRID 705031

반응식

HRID 705031 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 67513398HCID 67513398, 화합물

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178479802HCID 178479802, 화합물촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1298a6f452cc400ca0b63f7166fb57a9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173396B2

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