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

HRID 2195051Notes

Reaction equation

HRID 2195051 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, 0.13 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-7cdc8344a4cb4a049a8f96076d726abb
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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