Diisopropylethylamine → 1-[7-(2-bromo-4-trifluoromethylphenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl]piperidine-3-carbonitrile

HRID 1253826

Reaktionsgleichung

Reaktionsgleichung von HRID 1253826
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2[N:17]=[C:18]([CH3:22])[N:19]=[C:20](Cl)[C:15]=2[C:14]([CH3:23])=[C:13]1[CH3:24].[NH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([C:31]#[N:32])[CH2:26]1.C(N(CC)C(C)C)(C)C>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[N:12]1[C:16]2[N:17]=[C:18]([CH3:22])[N:19]=[C:20]([N:25]3[CH2:30][CH2:29][CH2:28][CH:27]([C:31]#[N:32])[CH2:26]3)[C:15]=2[C:14]([CH3:23])=[C:13]1[CH3:24]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 420926Piperidine-3-carbonitrileHCID 598455997-(2-bromo-4-trifluoromethylphenyl)-4-chloro-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 104583591-[7-(2-bromo-4-trifluoromethylphenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl]piperidine-3-carbonitrileAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 7-(2-bromo-4-trifluoromethylphenyl)-4-chloro-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine (400 mg), piperidine-3-carbonitrile (290 mg), N,N-diisopropylethylamine (309 mg) in ethanol (2 mL) was heated at reflux for 6 days. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=5:1) to obtain two diastereoisomers (low polar diastereoisomer: 62 mg and high polar diastereoisomer: 36 mg) of 1-[7-(2-bromo-4-trifluoromethylphenyl)-2,5,6-trimethyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl]piperidine-3-carbonitrile.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 days
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: hexane/ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-066e79911d3241909a30f995daca8da2
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455511B2

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