Trifluoroacetic acid → 6-fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-ylamine

HRID 1692851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692851
[F:1][C:2]1[N:7]=[C:6]([NH:8]CC2C=CC(OC)=CC=2)[CH:5]=[CH:4][C:3]=1[CH2:18][C:19]1[C:27]2[CH:26]=[N:25][CH:24]=[N:23][C:22]=2[NH:21][CH:20]=1.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:18][C:19]1[C:27]2[CH:26]=[N:25][CH:24]=[N:23][C:22]=2[NH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57963085[6-Fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(4-methoxy-benzyl)-amine

Produkt 1

HCID 579630566-fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-ylamineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To [6-fluoro-5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(4-methoxy-benzyl)-amine (P-0105, 4.5 g, 12.38 mmol) in 100 mL of dichloromethane, trifluoroacetic acid (95 mL, 1.238 mol) was added. The reaction was stirred at reflux for several hours, then concentrated under vacuum. The resulting material was taken up in ethyl acetate and poured into aqueous potassium carbonate. The resulting solid was filtered, washed with water, azeotroped from toluene and triturated with dichloromethane. The solid was isolated by filtration to provide the desired compound as a white solid (68, 2.8 g, 11.51 mmol, 93% yield).

Aufarbeitung

  1. temperatureat reflux for several hours
  2. concentrationconcentrated under vacuum
  3. additionpoured into aqueous potassium carbonate
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customazeotroped from toluene
  7. customtriturated with dichloromethane
  8. customThe solid was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-57598394aabd4155b9bdf2207ea5a5d1
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158636B2

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