Propargyl alcohol → 3-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-propyn-1-ol

HRID 1049842

Reaktionsgleichung

Reaktionsgleichung von HRID 1049842
Br[C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1.[O:12]1C[CH2:15][CH2:14][CH2:13]1.C(O)C#C.C(N(CC)C(C)C)(C)C>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:10][C:9]1[C:4]2[CH:3]=[C:2]([C:15]#[C:14][CH2:13][OH:12])[NH:11][C:5]=2[N:6]=[CH:7][N:8]=1

Komponenten

8

Edukt 4

HCID 7859Propargyl alcoholHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

Produkt 1

HCID 900835623-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-propyn-1-olAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture comprising 3.00 g (12.9 mmol) 6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS-No: 784150-41-0), 90 mL tetrahydrofuran, 3.0 mL prop-2-yn-1-ol, 246 mg copper(I) iodide, 746 mg tetrakis(triphenylphosphine)palladium(0) and 3.93 mL N,N-diisopropylethylamine was heated at 80° C. for 4 hours. Water was added and the mixture extracted with ethylacetate/methanol (8:2). The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvents the residue was purified by chromatography to give 833 mg (31%) of the title compound.

Aufarbeitung

  1. extractionthe mixture extracted with ethylacetate/methanol (8:2)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and removal of the solvents the residue
  5. customwas purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1618b8364f504ed0a1a3c6b0504bf920
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382255B2

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