2-(Methylamino)ethanol → 2-chloro-4-methyl-6-(N-methyl-2-hydroxyethylamino)pyrimidine

HRID 1251478Notes

Reaction equation

HRID 1251478 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][NH:11][CH2:12][CH2:13][OH:14]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:9])[CH:5]=[C:6]([N:11]([CH2:12][CH2:13][OH:14])[CH3:10])[N:7]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 183238282-chloro-4-methyl-6-(N-methyl-2-hydroxyethylamino)pyrimidineYield 34.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Part A: A solution of 2,4-dichloro-6-methylpyrimidine (1.0 g) and 2-(methylamino)ethanol (0.4 g) in ethanol (50 mL) was refluxed for 24 hours. The solvent was evaporated to give a crude residue, which was chromatographed on silica gel using 5% methanol in chloroform to yield 2-chloro-4-methyl-6-(N-methyl-2-hydroxyethylamino)pyrimidine (370 mg).

Workup

  1. customThe solvent was evaporated
  2. customto give a crude residue, which
  3. customwas chromatographed on silica gel using 5% methanol in chloroform

Sources & evidence

ORD record
ord-809df0f308944ae4b78afa458d165f64
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

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