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

HRID 1250175Notes

Reaction equation

HRID 1250175 reaction equation
[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[C:48]([CH2:49]O)=[N:47][CH:46]=[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:48]3[N:44]([CH3:43])[N:45]=[CH:46][N:47]=3)=[N:13][C:12]=12

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanolHCID 178518575HCID 178518575, compound

Product 1

HCID 112696063-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[1,5-alpha]pyrimidineYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Fluorophenyl)-6-phenyl-4H-1,2,3-triazolo[1,5-α]pyrimidin-5-one (10 mg, 0.033 mmol), triphenylphosphine (21 mg, 0.08 mmol) and (2-methyl-2H-1,2,4-triazol-3-yl)methanol (11 mg, 0.087 mmol) were suspended at room temperature in dry tetrahydrofuran (0.5 ml). Diethyl azodicarboxylate (15 μl, 0.095 mmol) was added at which point a clear yellow solution resulted. The reaction was stirred at room temperature for 64 hours before purification by preparative thin layer chromatography to afford 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[1,5-α]pyrimidine (5 mg, 39%) as a white solid. δH (400 MHz, CDCl3) 3.79 (3H, s, NMe, 5.69 (2H, s, OCH2), 7.24 (1H, td, J=9.2 and 1.2 Hz, ArH), 7.31 (1H, td, J=8.4 and 1.3 Hz, ArH), 7.39-7.43 (1H, m, ArH), 7.48-7.51 (3H, m, ArH), 7.54-7.58 (2H, m, ArH), 7.86 (1H, s, CH-triazole), 8.00 (1H, td, J=8.3 and 2.0 Hz, ArH), 8.80 (1H, s, PhC═CH);m/z (ES+) 402 (M+H+).

Workup

  1. customresulted

Sources & evidence

ORD record
ord-373cf203b9104724a5017eeec392cb13
Source dataset
uspto-grants-2002_01
Patent number
US06337331B1

Reaction notes

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