Hydrochloric Acid → N-(4-Formyl-2-pyrimidinyl)acetamide

HRID 325113Notes

Reaction equation

HRID 325113 reaction equation
C[O-].[Na+].C(O[O:8][CH:9](OC)[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[N:11]=1)(=O)C.Cl>CO>[C:17]([NH:16][C:12]1[N:11]=[C:10]([CH:9]=[O:8])[CH:15]=[CH:14][N:13]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 22002535HCID 22002535, compound

Product 1

HCID 17840022N-(4-Formyl-2-pyrimidinyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.056 g, 1.0 mmol) was added to a solution of 2-acetamidopyrimidine-4-carboxaldehyde monomethyl monoacetoxy acetal (5.0 g, 21 mmol) in MeOH (25 mL) at ambient temperature. After stirring at this temperature for 3 h, the reaction mixture was neutralized by addition of 3N HCl. The resulting solution was concentrated and the residue was treated with CH2Cl2. Remaining solids were removed by filtration and the solvent was evaporated to afford the title compound as a yellow solid; yield 3.2 g (92%).

Workup

  1. concentrationThe resulting solution was concentrated
  2. additionthe residue was treated with CH2Cl2
  3. customwere removed by filtration
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c2add1b08275486fb8df1c945bdbc93b
Source dataset
uspto-grants-2001_04
Patent number
US06222036B1

Reaction notes

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