Potassium Phosphate, Tribasic → 5-[4-(Benzyloxy)-3-methoxyphenyl]-3-chloro-6-methyl-1,2,4-triazine

HRID 1013075Notes

Reaction equation

HRID 1013075 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([CH3:9])=[C:6](Cl)[N:7]=1.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=1[O:27][CH3:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(COC)OC.C(Cl)(Cl)Cl>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:6]2[N:7]=[C:2]([Cl:1])[N:3]=[N:4][C:5]=2[CH3:9])=[CH:20][C:19]=1[O:27][CH3:28])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 106826034-(Benzyloxy)-3-methoxybenzeneboronic acidHCID 216981333,5-Dichloro-6-methyl-1,2,4-triazine

Product 1

HCID 584966165-[4-(Benzyloxy)-3-methoxyphenyl]-3-chloro-6-methyl-1,2,4-triazine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A degassed solution of 3,5-dichloro-6-methyl-1,2,4-triazine (151 mg, 0.9 mmol), 4-(benzyloxy)-3-methoxybenzene boronic acid (236 g, 0.9 mmol), tetralis(triphenylphosphine)palladium(0) (55 mg, 0.05 mmol) and tripotassium phosphate (249 mg, 1.2 mmol) in dimethoxyethane (5 mL) was heated at reflux for 24 h. Upon cooling to room temperature the solution was diluted with CHCl3 and filtered through Celite®. The filtrate was concentrated in vacuo and the product purified by column chromatography using ethyl acetate-hexane (25:75) as eluent to furnish (75 mg, 22%).

Workup

  1. temperatureat reflux for 24 h
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe product purified by column chromatography
  5. customto furnish (75 mg, 22%)

Sources & evidence

ORD record
ord-cac6f7bc1b2f485eba282fa50e5cd8c7
Source dataset
uspto-grants-2011_07
Patent number
US07981900B2

Reaction notes

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