Chloroacetone → 6-Bromo-2-methylimidazo[1,2-a]pyrimidine

HRID 500730Notes

Reaction equation

HRID 500730 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.Cl[CH2:10][C:11](=O)[CH3:12].C(OCC)(=O)C>CC(O)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([CH:10]=[C:11]([CH3:12])[N:8]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 6571ChloroacetoneHCID 8857Ethyl AcetateHCID 2313102-Amino-5-bromopyrimidine

Product 1

HCID 401523416-Bromo-2-methylimidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 5-bromopyrimidin-2-amine (170.0 g, 0.98 mol) in i-PrOH (2 L) and DMF (500 mL) was added 1-chloropropan-2-one (606 g, 6.53 mol), then the mixture was stirred at 10° C. for 16 h. TLC (petroleum ether:ethyl acetate=1:2) showed the reaction was complete. The reaction mixture was quenched by Na2CO3 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1) to afford compound B-8-2 (10.0 g, 4.8%) as a yellow solid.

Workup

  1. customThe reaction mixture was quenched by Na2CO3
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=5:1)
  5. customto afford compound B-8-2 (10.0 g, 4.8%) as a yellow solid

Sources & evidence

ORD record
ord-44b73b79a8ed4b1aa3fb19a067c0d927
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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