2-Methylpyrrolidine → 4,6-Dichloro-2-(2-methylpyrrolidin-1-yl)pyrimidine

HRID 1444117Notes

Reaction equation

HRID 1444117 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(=O)(O)[O-].[Na+].[CH3:15][CH:16]1[CH2:20][CH2:19][CH2:18][NH:17]1>CO>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([N:17]2[CH2:18][CH2:19][CH2:20][CH:16]2[CH3:15])[N:3]=1

Participants

5

Reactant 3

HCID 130032-MethylpyrrolidineHCID 773782,4,6-TrichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 574290204,6-Dichloro-2-(2-methylpyrrolidin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2,4,6-trichloropyrimidine (23.5 g, o.13 mol) in anhydrous MeOH (220 mL), and add solid sodium bicarbonate (28.3 g, 0.33 mol). Cool to 0° C. and add 2-methylpyrrolidine (12 g, 0.14 mol) dropwise. Let stir at room temperature for 16 h. Filter off the excess sodium bicarbonate, and evaporate under reduced pressure. Purify by SiO2 liquid chromatography, using 50:1 hexanes:EtOAc, increasing to 30:1 hexanes:EtOAc, to provide the title compound as a white solid.

Workup

  1. filtrationFilter off the excess sodium bicarbonate
  2. customevaporate under reduced pressure
  3. customPurify by SiO2 liquid chromatography
  4. temperatureEtOAc, increasing to 30:1 hexanes

Sources & evidence

ORD record
ord-96c66e98638440aba3600906e43156c1
Source dataset
uspto-grants-2010_02
Patent number
US07662830B2

Reaction notes

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