Potassium Carbonate → HCID 67326673, compound

HRID 1500744Notes

Reaction equation

HRID 1500744 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=1.[C:23]([C:25]1[N:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][N:26]=1)#[CH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:32][O:31][C:29]1[CH:28]=[CH:27][N:26]=[C:25]([C:23]2[CH:24]=[N:14][N:15]3[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][C:16]=23)[N:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10011938Pyrimidine, 2-ethynyl-4-methoxy- (9CI)HCID 12291499HCID 12291499, compound

Product 1

HCID 67326673HCID 67326673, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Amino-4-cyanopyridinium 2,4,6-trimethylbenzenesulfonate (Preparation 2, 12.10 g, 37.88 mmol) was added in portions over 6 hours to a stirred suspension of 2-ethynyl-4-methoxypyrimidine (Preparation 1b, 2.54 g, 18.94 mmol) and potassium carbonate (3.93 g, 28.43 mmol) in anhydrous N,N′-dimethylformamide (47 mL) at 0° C. and the resulting mixture was stirred at ambient temperature for 48 hours. The solvent was evaporated and dichloromethane was added to the residue. The solid formed was filtered and the filtrate evaporated to dryness. The crude product was purified by flash chromatography (4:1 hexanes/ethyl acetate) to give the title compound (3.51 g, 74%) as a solid.

Workup

  1. customThe solvent was evaporated
  2. additiondichloromethane was added to the residue
  3. customThe solid formed
  4. filtrationwas filtered
  5. customthe filtrate evaporated to dryness
  6. customThe crude product was purified by flash chromatography (4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-5ffa381ac93e4e069d49d3fd198ea282
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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