Isopropanol → 6-Bromo-2,3-dimethylimidazo[1,2-a]pyrimidine

HRID 500731Notes

Reaction equation

HRID 500731 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.C(O[CH2:13][CH3:14])(=O)C.[CH3:15][CH:16](O)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([C:13]([CH3:14])=[C:15]([CH3:16])[N:8]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 2313102-Amino-5-bromopyrimidine

Product 1

HCID 401523436-Bromo-2,3-dimethylimidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromopyrimidin-2-amine (400 g, 2.2 mol) in i-PrOH (2 L) and DMF (500 mL) was added compound B-9-2 (400 g, 2.6 mol), the resulting mixture was stirred at 100° C. for 20 hrs. TLC (petroleum ether:ethyl acetate=1:1) showed the reaction was complete, the reaction mixture was quenched by addition of aqueous Na2CO3 and filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=1:1) to afford compound B-9-4 (12.0 g, 2.4%) as a yellow solid.

Workup

  1. customthe reaction mixture was quenched by addition of aqueous Na2CO3
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=1:1)
  5. customto afford compound B-9-4 (12.0 g, 2.4%) as a yellow solid

Sources & evidence

ORD record
ord-1249640998b94361ab4e8d03b8fb9d9a
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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