Potassium Carbonate → HCID 70160253, compound

HRID 2227281Notes

Reaction equation

HRID 2227281 reaction equation
COP([CH2:7][C:8](=[O:25])[CH2:9][N:10]1[C@H:14]([CH3:15])[CH2:13][C@H:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:11]1=[O:24])(=O)OC.C(=O)([O-])[O-].[K+].[K+].[CH3:32][C:33]1[N:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][N:34]=1>C1COCC1.C(OCC)(=O)C>[C:20]([O:19][C:17](=[O:18])[NH:16][C@H:12]1[CH2:13][C@@H:14]([CH3:15])[N:10]([CH2:9][C:8](=[O:25])[CH:7]=[CH:39][C:36]2[CH:35]=[N:34][C:33]([CH3:32])=[N:38][CH:37]=2)[C:11]1=[O:24])([CH3:21])([CH3:22])[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 86758298HCID 86758298, compound

Product 1

HCID 70160253HCID 70160253, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of 4-3 (2.5 g, 6.61 mmol), potassium carbonate (1.83 g, 13.2 mmol), and 2-methyl-pyrimidine-5-carboxaldehyde (for preparation, see U.S. Pat. No. 6,048,861) (0.81 g, 6.61 mmol) in THF (50 mL) was heated at 60-65° C. for 3 hours and then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, dried over magnesium sulfate, and filtered. Following evaporative removal of the solvent, the residue was purified by flash column chromatography (silica gel, 95:5% ethyl acetate/methanol) to give 5-1 as a white foam.

Workup

  1. customfor preparation
  2. washwashed with saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customremoval of the solvent
  6. customthe residue was purified by flash column chromatography (silica gel, 95:5% ethyl acetate/methanol)

Sources & evidence

ORD record
ord-42d8ad6441564adfaa3ae4bc8c1d0836
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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