Hydrochloric Acid → 2-Aminopyrimidine-4-carbaldehyde

HRID 552114Notes

Reaction equation

HRID 552114 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH2:10])[N:5]=1.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[NH2:10][C:6]1[N:5]=[C:4]([CH:3]=[O:2])[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 49130324-(dimethoxymethyl)pyrimidin-2-amine

Product 1

HCID 178323462-Aminopyrimidine-4-carbaldehydeYield 37.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.5 g (15 mmol, 1.0 eq.) of 2-aminopyrimidine-4-carboxaldehyde dimethylacetal (I-8) in 16 mL (48 mmol, 3.2 eq.) of 3M HCl was heated at 48° C. for 14 h. The mixture was allowed to cool to room temperature and diluted with 50 mL of EtOAc. The aqueous layer was neutralized with NaHCO3 and then extracted with EtOAc (5×50 mL). The combined organic extracts were dried (Na2SO4) and the solvent removed in vacuo to provide 0.69 g (5.6 mmol, 37%) of 2-aminopyrimidine-4-carboxaldehyde (I-9) as a yellow solid.

Workup

  1. extractionextracted with EtOAc (5×50 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8d1c69c2c51a44118c5950aa007bf96e
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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