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

HRID 509614Notes

Reaction equation

HRID 509614 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): δ 7.84 (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-097486aaa3d04d9aa518e430b239ef08
Source dataset
uspto-grants-2015_08
Patent number
US09096589B2

Reaction notes

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