Hydrochloric Acid → 2-Aminopyrimidine-4-carbaldehyde

HRID 605862Notes

Reaction equation

HRID 605862 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 37.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2.5 g (15 mmol, 1.0 eq.) 2-aminopyrimidine-4-carboxaldehyde dimethylacetal in 16 ml (45 mmol, 3 eq.) of 3M HCl was heated at 48° C. for 14 h. The mixture was cooled to r.t. and layered with 50 mL of EtOAc. The aqueous layer was neutralized with NaHCO3 and then extracted with EtOAc (5×50 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo afford 0.69 g (37%) of 2-aminopyrimidine-4-carboxaldehyde.

Workup

  1. extractionextracted with EtOAc (5×50 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4aa597910cc4dcab949b870cd5bf2ef
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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