Dimethylamine, hydrochloride → 2,6-Dichloro-N,N-dimethylpyrimidin-4-amine

HRID 586412Notes

Reaction equation

HRID 586412 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[Cl:5][C:6]1[N:11]=[C:10]([Cl:12])[CH:9]=[C:8](Cl)[N:7]=1>C(Cl)Cl>[Cl:5][C:6]1[N:7]=[C:8]([N:3]([CH3:4])[CH3:2])[CH:9]=[C:10]([Cl:12])[N:11]=1

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 154386932,6-Dichloro-N,N-dimethylpyrimidin-4-amineYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dimethylamine hydrochloride (35.6 g, 0.44 mol) was added to a vigorous stirring solution of 2,4,6-trichloropyrimidine (80.0g, 0.44 mol) in CH2Cl2 (1.5 L) at −78° C. Triethylehtylmine (88.2 g, 0.87 mol) was added dropwise to the above mixture and stirred for 3 hours at −78° C. The resulting mixture was brought to 0° C. over a period of 3 hours and the reaction was then quenched with water (250 mL). The organic layer was separated, washed with aqueous citric acid (2×100 mL), brine (2×200 mL), dried over Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography [eluent: EtOAc/hexanes (1:9)], giving the desired product (59.9 g, 60%).

Workup

  1. additionTriethylehtylmine (88.2 g, 0.87 mol) was added dropwise to the above mixture
  2. waitThe resulting mixture was brought to 0° C. over a period of 3 hours
  3. customthe reaction was then quenched with water (250 mL)
  4. customThe organic layer was separated
  5. washwashed with aqueous citric acid (2×100 mL), brine (2×200 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography [eluent: EtOAc/hexanes (1:9)]

Sources & evidence

ORD record
ord-01979f3b6b9b4208bc613965e04957d7
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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