Phosphorus oxychloride → 4-Chloro-7-(2-chlorophenyl)-8-iodo-2-methylpyrazolo[1,5-a][1,3,5]triazine

HRID 2054384Notes

Reaction equation

HRID 2054384 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:18]([I:19])=[C:11]2[NH:12][C:13]([CH3:17])=[N:14][C:15](=O)[N:10]2[N:9]=1.C(N(C(C)C)CC)(C)C.O=P(Cl)(Cl)[Cl:31]>C1(C)C=CC=CC=1>[Cl:31][C:15]1[N:10]2[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:18]([I:19])=[C:11]2[N:12]=[C:13]([CH3:17])[N:14]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178433495HCID 178433495, compound

Product 1

HCID 596556974-Chloro-7-(2-chlorophenyl)-8-iodo-2-methylpyrazolo[1,5-a][1,3,5]triazineYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 7-(2-chlorophenyl)-8-iodo-2-methyl-1H-pyrazolo[1,5-a][1,3,5]triazin-4-one (I-1A-1d; 1.00 g, 2.6 mmol) and diisopropylethylamine (0.68 ml, 3.8 mmol) in toluene (30 ml) at room temperature was added POCl3 (1.28 ml, 14 mmol), dropwise. The mixture was heated at reflux for 5 hours, cooled to room temperature, and then concentrated, in vacuo, to a viscous oil. The residue was then purified by passing through a plug of silica gel on a sintered glass funnel using 20% ethyl acetate in hexanes as eluant to provide I-1A-1e as a yellow solid (0.93 g, 89%): +APcI MS (M+1) 316.3; 1H NMR (400 MHz, CD2Cl2) δ 7.57 (d, J=7.9 Hz, 1H), 7.53-7.43 (m, 3H), 2.74 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. concentrationconcentrated, in vacuo, to a viscous oil
  4. customThe residue was then purified

Sources & evidence

ORD record
ord-668088c5f2094c7ca6396711e449fe21
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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