N,N-Diethylaniline → 5-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 2173532Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173532
[C:1]([C:5]1[NH:10][C:9]2[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:12]=[N:13][C:8]=2[C:7](=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C1C=CC=CC=1)C.O=P(Cl)(Cl)[Cl:37]>>[C:1]([C:5]1[N:6]=[C:7]([Cl:37])[C:8]2[N:13]=[N:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178490918HCID 178490918, Verbindung

Produkt 1

HCID 866832995-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Versuchsvorschrift

A mixture of 5-tert-butyl-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one (50.0 mg, 160 μmol) and N,N-diethylaniline (50.8 μL, 319 μmol) in POCl3 (1000 μL, 10.9 mmol) was refluxed for 4 h under N2 atmosphere. The reaction mixture was concentrated in vacuo, diluted with EtOAc, washed with cold H2O and brine, dried over Na2SO4 and concentrated in vacuo to afford crude 5-tert-butyl-7-chloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine. The residue was used for the next reaction without further purification.

Aufarbeitung

  1. temperaturewas refluxed for 4 h under N2 atmosphere
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with EtOAc
  4. washwashed with cold H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-230a6e79978d43b9bd25335522c41e22
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056866B2

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