Dimethylformamide → imidazo[1,2-a]pyrimidine-3-carbaldehyde

HRID 648454Notes

Reaction equation

HRID 648454 reaction equation
P(Cl)(Cl)(Cl)=O.O1[C:10](=O)[CH:9]=[NH+:8][N-]1.[CH:12]([C:14]1[C:18](=[O:19])O[N-][N+:15]=1[CH3:20])=O.[OH-].[Na+].[CH3:23][N:24](C=O)C>>[CH:18]([C:14]1[N:15]2[CH:20]=[CH:10][CH:9]=[N:8][C:23]2=[N:24][CH:12]=1)=[O:19]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178482033HCID 178482033, compound

Product 1

HCID 404535imidazo[1,2-a]pyrimidine-3-carbaldehyde

Procedure

To 14 ml DMF cooled to 0° was added 6.0 g (0.039 mol) phosphorus oxychloride dropwise over 15 minutes, followed by 1.79 g (0.015 mol) imidazo[1,5-a]pyrimidine (1). The resulting mixture was heated at 120° for 0.5 hours and then at 90° for 5 hours. The cooled reaction mixture was then poured onto a mixture of ice water, made basic with 40% NaOH solution and then extracted with 4×100 ml portions of CH2Cl2. The combined organic extracts were dried and the solvent removed in vacuo to give crude (2). This was purified by chromatography on silica gel eluting with CH2Cl2 (97)-isopropanol (3) to give pure (2), m.p. 198°-200°.

Workup

  1. temperatureThe resulting mixture was heated at 120° for 0.5 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with 4×100 ml portions of CH2Cl2
  4. customThe combined organic extracts were dried
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-674571112073425fb683f637171df40d
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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