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Trifluoroacetic acid → 5-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1692842
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1692842
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([C:11]2[C:19]3[CH:18]=[N:17][CH:16]=[N:15][C:14]=3[N:13]([Si](C(C)C)(C(C)C)C(C)C)[CH:12]=2)O)=[CH:5][N:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]([CH2:9][C:11]2[C:19]3[CH:18]=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)=[CH:7][N:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57963217(2-methylsulfanyl-pyrimidin-5-yl)-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

Produkt 1

HCID 579631715-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidineAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (2-methylsulfanyl-pyrimidin-5-yl)-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (55, 2.75 g, 6.40 mmol) in 50.0 mL of 1,2-dichloroethane, triethylsilane (8.00 mL, 50.1 mmol) and trifluoroacetic acid (4.00 mL, 51.9 mmol) were added. The reaction was heated at 80° C. overnight, then concentrated under vacuum, combined with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 2-15% methanol in dichloromethane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (56, 1.20 g). MS (ESI) [M+H+]+=258.2.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 2-15% methanol in dichloromethane
  8. customthe solvents removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f8eb45e78ab342d49284d6e8eb5b6772
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08158636B2

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