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

HRID 537889Notes

Reaction equation

HRID 537889 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-29ded83cce7145df887ef8f67432a690
Source dataset
uspto-grants-2014_10
Patent number
US08865711B2

Reaction notes

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