Ethyl Acetate → Imidazo[1,2-A]pyrimidine-7-carbaldehyde

HRID 2183877Notes

Reaction equation

HRID 2183877 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][N:7]2[CH:10]=[CH:11][N:12]=[C:6]2[N:5]=1.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>Cl.O>[N:12]1[CH:11]=[CH:10][N:7]2[CH:8]=[CH:9][C:4]([CH:3]=[O:2])=[N:5][C:6]=12

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 180012957-Dimethoxymethylimidazo[1,2-a]pyrimidine

Product 1

HCID 18001283Imidazo[1,2-A]pyrimidine-7-carbaldehydeYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
48 °C

Procedure

7-Dimethoxymethylimidazo[1,2-α]pyrimidine (1.00 g, 5.18 mmol) was dissolved in 3N hydrochloric acid and heated at 48° C. for 14 h. The solution was layered with ethyl acetate (30 ml) and solid sodium hydrogencarbonate (1.06 g, 12.6 mmol) was added in portions over 5 min. The mixture was diluted with water (6 ml) and extracted with dichloromethane (5×50 ml). The combined organics were dried over anhydrous sodium sulfate, filtered and evaporated to give imidazo[1,2-α]pyrimidine-7-carbaldehyde (749 mg, 99%) as a yellow solid: δH (360 MHz, CDCl3) 7.53 (1H, d, J 7), 7.77 (1H, d, J 1), 8.10 (1H, d, J 1), 8.60 (1H, d, J 7), 10.05 (1H, s).

Workup

  1. additionwas added in portions over 5 min
  2. extractionextracted with dichloromethane (5×50 ml)
  3. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f44122b4021e443d8a6e7fa943ff0f37
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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