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

HRID 1250182Notes

Reaction equation

HRID 1250182 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.[CH2:43]([N:45]1[C:49]([CH2:50]O)=[N:48][CH:47]=[N:46]1)[CH3:44].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:43]([N:45]1[C:49]([CH2:50][O:23][C:14]2[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:16][N:11]3[N:10]=[N:9][C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[C:12]3[N:13]=2)=[N:48][CH:47]=[N:46]1)[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11412385(1-ethyl-1H-1,2,4-triazol-5-yl)methanolHCID 178518575HCID 178518575, compound

Product 1

HCID 544396535-(2-ethyl-2H-1,2,4-triazol-3-ylmethoxy)-3-(2-fluorophenyl)-6-phenyl-1,2,3-triazolo[1,5-alpha]pyrimidineYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Fluorophenyl)-6-phenyl-4H-1,2,3-triazolo[1,5-α]pyrimidin-5-one (95 mg, 0.31 mmol), triphenylphosphine (203 mg, 0.78 mmol) and (2-ethyl-2H-1,2,4-triazol-3-yl)methanol (110 mg, 0.78 mmol) were suspended in dry tetrahydrofuran (1,5 ml). Diethyl azodicarboxylate (123 μl, 0.78 mmol) was added and a solution resulted immediately. The reaction was stirred at room temperature for 16 hours before purification by preparative tlc (40% EtOAc/hexanes) to give a white solid which was recrystallised from ethyl acetate/hexanes and triturated with diethyl ether to afford 5-(2-ethyl-2H-1,2,4-triazol-3-ylmethoxy)-3-(2-fluorophenyl)-6-phenyl-1,2,3-triazolo[1,5-α]pyrimidine (67 mg, 52%) as white plates, m.p. 147-148° C.; δH (400 MHz, CDCl3) 1.22 (3H, t, J=7.3 Hz, NCH2CHH3), 4.13 (2H, q, J=7.3 Hz, NCH2CH3), 5.70 (2H, s, OCH2), 7.24 (1H, t, J=29.3 Hz, ArH), 7.31 (1H, t, J=7.5 Hz. ArH), 7.41-7.48 (4H, m, ArH, 7.54-7.56 (2H, m, ArH), 7.89 (1H, s, triazole CH), 8.02 (1H, td, J=7.5 and 1.7 Hz, ArH), 8.79 (1H, s, pyrimidine CH); m/z (ES+) 416 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-db0a635ad1cd42d6aeb95fbbaf2c71fc
Source dataset
uspto-grants-2002_01
Patent number
US06337331B1

Reaction notes

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