1,3-Dichloroacetone → 2-(Chloromethyl)-5,7-dimethylimidazo[1,2-a]pyrimidine

HRID 1094031Notes

Reaction equation

HRID 1094031 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][CH2:11][C:12](=O)[CH2:13]Cl>COCCOC>[Cl:10][CH2:11][C:12]1[N:1]=[C:2]2[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]2[CH:13]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 130212-Amino-4,6-dimethyl pyrimidine

Product 1

HCID 6933302-(Chloromethyl)-5,7-dimethylimidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 2-amino-4,6-dimethylpyrimidine (2.46 g, 20.0 mmol) and 1,3-dichloro-2-propanone (2.67 g, 21.0 mmol) in 1,2-dimethoxyethane (20 mL) was stirred at 45° C. overnight. A precipitate formed, and this was collected by filtration, and was then refluxed with ethanol (15 mL) for 2 hours. After cooling to room temperature, the product precipitated as white needles which were collected by filtration and vacuum dried to yield the title compound pure as its hydrochloride salt (883 mg, 19%). 1H NMR (500 MHz, DMSO-d6): δ7.84 (s, 1H), 6.88 (s, 1H), 4.84 (s, 2H), 2.60 (s, 3H), 2.49 (s, 3H).

Workup

  1. customA precipitate formed
  2. filtrationthis was collected by filtration
  3. temperaturewas then refluxed with ethanol (15 mL) for 2 hours
  4. customthe product precipitated as white needles which
  5. filtrationwere collected by filtration and vacuum
  6. customdried

Sources & evidence

ORD record
ord-960242ca42724973ba1651581cfb3e29
Source dataset
uspto-grants-2012_03
Patent number
US08133897B2

Reaction notes

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