Triphenylphosphine → 3-(2-fluorophenyl)-5-(1-methyl-1H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[1,5-alpha]pyrimidine

HRID 1250181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250181
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:23])[NH:13][C:12]=12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:43][N:44]1[CH:48]=[N:47][C:46]([CH2:49]O)=[N:45]1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([O:23][CH2:49][C:46]3[N:47]=[CH:48][N:44]([CH3:43])[N:45]=3)=[N:13][C:12]=12

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10351670(1-Methyl-1H-1,2,4-triazol-3-yl)methanolHCID 178518575HCID 178518575, Verbindung

Produkt 1

HCID 1317230833-(2-fluorophenyl)-5-(1-methyl-1H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[1,5-alpha]pyrimidineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-(2-Fluorophenyl)-6-phenyl-4H-1,2,3-triazolo[1,5-α]pyrimidin-5-one (77 mg, 0.25 mmol), triphenylphosphine (165 mg, 0.63 mmol) and (1-methyl-1H-1,2,4-triazol-3-yl)methanol (80 mg, 0.63 mmol) were suspended in dry tetrahydrofuran (1.5 ml). Diethyl azodicarboxylate (100 μl, 0.63 mmol) was added and a solution resulted immediately. The reaction was stirred at room temperature for 48 hours before purification by preparative tlc (40% EtOAc/hexanes) to give a white solid which was recrystallised from ethyl acetate/hexanes to afford 3-(2-fluorophenyl)-5-(1-methyl-1H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[1,5-α]pyrimidine (49 mg, 49%) as white needles, m.p. 170-171° C.; δH (400 MHz, d6-DMSO) 3.84 (3H, s, NCH3), 5.57 (2H, s, OCH2), 7.35-7.41 (2H, m, ArH), 7.43-7.51 (4H, m, ArH), 7.73 (2H, dd, J=8.1 and 1.8 Hz, ArH), 8.14 (1H, td, J=7.5 and 1.8 Hz, ArH), 8.45 (1H, s, triazole CH), 9.51 (1H, s, pyrimidine CH); m/z (ES+) 402 (M+H+).

Aufarbeitung

  1. customa solution resulted immediately
  2. customto give a white solid which
  3. customwas recrystallised from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2c11cd99b16047a89b58f3f3dc0aae5d
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06337331B1

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