Potassium Carbonate → HCID 86713559, compound

HRID 524027

Reaction equation

HRID 524027 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([O-:14])=O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH2:15][C:16]1[C:21]([CH:22]=O)=[CH:20][N:19]=[C:18]([S:24][CH3:25])[N:17]=1.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[C:12](=[O:14])[N:15]([CH3:26])[C:16]3[N:17]=[C:18]([S:24][CH3:25])[N:19]=[CH:20][C:21]=3[CH:22]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 69507942-(3,5-Dimethoxyphenyl)acetate

Product 1

HCID 86713559HCID 86713559, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(3,5-dimethoxyphenyl)acetate (6) (440 mg, 2.40 mmol), 4-amino-2-(methylthio)pyrimidine-5-carbaldehyde (4) (605 mg, 2.88 mmol) and potassium carbonate (662 mg, 4.8 mmol) in DMF (30 mL) was stirred at 110° C. for 3 hours. The reaction was monitored by LCMS. The reaction mixture was diluted with H2O (30 mL), and extracted by EtOAc (3×40 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/EtOAc=2:1) to afford 6-(3,5-dimethoxyphenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (7) (683 mg, 83%) as a white solid. MS (ES+) C17H17N3O5S requires: 343. found: 344 [M+H]+.

Workup

  1. extractionextracted by EtOAc (3×40 mL)
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/EtOAc=2:1)

Sources & evidence

ORD record
ord-9f38157d1275451eb51109fea4fbfcb4
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Linked notes

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