2-Chloro-4,6-dimethoxy-1,3,5-triazine → 2,4-dimethoxy-6-phenyl-1,3,5-triazine

HRID 1795382Notes

Reaction equation

HRID 1795382 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:10]1[N:15]=[C:14]([O:16][CH3:17])[N:13]=[C:12]([O:18][CH3:19])[N:11]=1>C1COCC1>[C:1]1([C:10]2[N:15]=[C:14]([O:16][CH3:17])[N:13]=[C:12]([O:18][CH3:19])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 178418255HCID 178418255, compound

Product 1

HCID 289642,4-dimethoxy-6-phenyl-1,3,5-triazineYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenylmagnesium bromide (1M in THF, 3.9 mL, 3.9 mmol) is added to a solution of 2-chloro-4,6-dimethoxy-1,3,5-triazine (300 mg, 1.70 mmol) and Fe(acac)3 (30 mg, 0.085 mmol) in THF (10 mL) at −30° C. After stirring for 30 min at that temperature, the reaction is quenched with brine, the aqueous layer is extracted with Et2O, the combined organic phases are dried over Na2SO4 and evaporated, and the residue is purified by flash chromatography (hexane/ethyl acetate, 10:1). After eluting a first fraction containing biphenyl (103 mg), one obtains 2-phenyl-4,6-dimethoxy-1,3,5-triazine as a colorless solid (231 mg, 63%). 1H NMR (300 MHz, CD2Cl2) δ 8.47 (d, 2H), 7.47–7.56 (m, 3H), 4.08 (s, 3H). 13C NMR (75 MHz, CD2Cl2) δ 175.0, 173.3, 135.6, 133.0, 129.2, 128.8, 55.4.

Workup

  1. customthe reaction is quenched with brine
  2. extractionthe aqueous layer is extracted with Et2O
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. customevaporated
  5. customthe residue is purified by flash chromatography (hexane/ethyl acetate, 10:1)
  6. washAfter eluting a first fraction
  7. additioncontaining biphenyl (103 mg), one

Sources & evidence

ORD record
ord-978245d45ccf4674899600f0cbe79a1b
Source dataset
uspto-grants-2006_04
Patent number
US07026478B2

Reaction notes

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