Chloroacetaldehyde → Imidazo[1,2-A]pyrimidin-7-amine

HRID 1411779Notes

Reaction equation

HRID 1411779 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3][C:2]=1[NH2:8].Cl[CH2:10][CH:11]=O>C(O)C.C([O-])(O)=O.[Na+]>[N:8]1[CH:10]=[CH:11][N:1]2[CH:6]=[CH:5][C:4]([NH2:7])=[N:3][C:2]=12

Participants

5

Reactant 2

HCID 33ChloroacetaldehydeHCID 674312,4-Diaminopyrimidine

Product 1

HCID 23000364Imidazo[1,2-A]pyrimidin-7-amineYield 60.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To the solution of pyrimidine-2,4-diamine (3.0 g, 0.027 mol) in ethanol (90 mL) and aqueous NaHCO3 (2M, 20 mL) was added 2-chloroacetaldehyde (4.3 g, 0.055 mol). The mixture was stirred at 70° C. overnight. TLC showed the starting material disappeared. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (3×30 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 1:5 petroleum ether/ethyl acetate to afford 199a as a white solid (2.2 g, 60%). MS: [M+H]+ 135.1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate (3×30 mL)
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica-gel column chromatography
  5. washeluting with 1:5 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-58995442b642456bb3ee7f4f529dede3
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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