Cyanuric chloride → 4-chloro-N-(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1948735Notes

Reaction equation

HRID 1948735 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].C[Mg]Br.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.[CH3:23]CN(C(C)C)C(C)C>C(Cl)Cl>[Cl:3][C:2]1[N:1]=[C:8]([CH3:23])[N:7]=[C:5]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)[N:4]=1

Participants

6

Reactant 4

HCID 7954Cyanuric chlorideHCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 178418573HCID 178418573, compound

Product 1

HCID 595483604-chloro-N-(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of cyanuric chloride (3.69 g, 20 mmol) in DCM (100 mL) at −10° C. was added methylmagnesium bromide (20 mL, 60 mmol, 3.0M solution in ether) maintaining the temperature at −10° C. The reaction was stirred for 4 h at −10° C. and then quenched with saturated ammonium chloride solution (20 mL). The organic layer was separated, dried (MgSO4) and filtered. The filtrate was cooled to 0° C. before the addition of 4-methoxybenzylamine (2.74 g, 20 mmol) and DIPEA (2.6 g, 20 mmol) took place. The reaction was stirred for 18 h at r.t. The organic layer was washed with water (2×20 mL), separated, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was crystallised from diisopropyl ether affording the title compound as a pale yellow solid (2.8 g, 51%). δH (CDCl3) 7.23 (d, J 9.2 Hz, 2H), 6.85 (d, J 9.2 Hz, 2H), 5.62 (br s, 1H), 4.56 (d, J 8.1 Hz, 2H), 3.79 (s, 3H), 2.38 (s, 3H). LCMS (ES+) 265 (M+H)+, RT 2.80 minutes (Method 5).

Workup

  1. customquenched with saturated ammonium chloride solution (20 mL)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. stirringThe reaction was stirred for 18 h at r.t
  6. washThe organic layer was washed with water (2×20 mL)
  7. customseparated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customThe residue was crystallised from diisopropyl ether affording the title compound as a pale yellow solid (2.8 g, 51%)
  12. customLCMS (ES+) 265 (M+H)+, RT 2.80 minutes (Method 5)

Sources & evidence

ORD record
ord-d430b4b2b6f2460e83f0ccd1d7fbb8dd
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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