Isopropyl Acetate → 2-Methoxypyrimidine-5-carboxaldehyde

HRID 657750Notes

Reaction equation

HRID 657750 reaction equation
S(O)(O)(=O)=O.[CH3:6][O:7][C:8](=[NH:10])[NH2:9].C[O:12][C:13](=N)N.C[NH+]([CH2:19][C:20](CN(C)C)=[CH:21][NH+](C)C)C.C(OC(C)C)(=O)C.C(=O)(O)[O-].[K+]>O>[CH3:6][O:7][C:8]1[N:9]=[CH:21][C:20]([CH:13]=[O:12])=[CH:19][N:10]=1

Participants

6

Reactant 4

HCID 7915Isopropyl AcetateHCID 516893Potassium BicarbonateHCID 11357018Bis(2-methylisouronium) sulphateHCID 101612644Vinamidinium

Product 1

HCID 31518662-Methoxypyrimidine-5-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred slurry of O-methylisourea hemisulfate (1.08 g, 4.13 mmol), vinamidinium salt (3.00 g, 8.26 mmol), 1-methylethyl acetate (16.0 mL, 137 mmol) was added a solution of potassium bicarbonate (1.17 g, 11.6 mmol) in water (5.0 mL) over a 10 minutes period. After completion of the addition the resulting reaction mixture was stirred at room temperature for 40 hours. The mixture was diluted with water (20 mL) and extracted with EtOAc (2×25 mL). The combined organic layers were dried over sodium sulfate and concentrated to yield a white solid.

Workup

  1. additionAfter completion of the addition
  2. customthe resulting reaction mixture
  3. extractionextracted with EtOAc (2×25 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto yield a white solid

Sources & evidence

ORD record
ord-fe6c5ecaa1a94111831f0dae382a8cf6
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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