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

HRID 2195080Notes

Reaction equation

HRID 2195080 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][C@H: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][C@@H:16]2[CH3:15])[N:3]=1

Participants

5

Reactant 3

HCID 773782,4,6-TrichloropyrimidineHCID 516892Sodium BicarbonateHCID 6999702(2S)-2-methylpyrrolidine

Product 1

HCID 591682744,6-Dichloro-2-(2-(S)-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-(S)-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 flash 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 flash chromatography
  4. temperatureEtOAc, increasing to 30:1 hexanes

Sources & evidence

ORD record
ord-cb545ec08cda4598838ee69a3cdb9a4d
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

Loading…