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

HRID 230957Notes

Reaction equation

HRID 230957 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.O>[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

6

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 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To an ice-cold solution containing 2,4,6-trichloropyrimidine (8 g, 44 mmol) in MeOH (80 mL) and NaHCO3 (10 g) add slowly and dropwise a methanolic solution (20 mL) of 2-methylpyrrolidine (46 mmol). Allow the mixture to warm to 25° C. and stir overnight. Dilute with water, vigorously stir for 1 hour, and filter to give white crystalline solid as a mixture of regioisomers. Chromatograph the mixture using flash column chromatography (ethyl acetate/hexanes eluent systems) to give 4,6-dichloro-2-(2-methyl-pyrrolidin-1-yl)-pyrimidine.

Workup

  1. additionadd slowly
  2. stirringvigorously stir for 1 hour
  3. filtrationfilter
  4. customto give white crystalline solid
  5. additionas a mixture of regioisomers

Sources & evidence

ORD record
ord-afddbe7fbda8467c8dbaa51e78a4f17f
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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