Potassium Carbonate → 1-(2-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-yl)ethyl)pyrrolidin-2-one

HRID 1930719Notes

Reaction equation

HRID 1930719 reaction equation
O=[C:2]([CH:11]1[C:16](=O)[CH2:15][CH2:14][O:13][CH2:12]1)[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:32][C:33]([NH2:35])=[NH:34])[CH:23]=[CH:24][C:25]=1[N:26]1[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([NH:32][C:33]2[N:35]=[C:2]([CH2:3][CH2:4][N:5]3[CH2:9][CH2:8][CH2:7][C:6]3=[O:10])[C:11]3[CH2:12][O:13][CH2:14][CH2:15][C:16]=3[N:34]=2)[CH:23]=[CH:24][C:25]=1[N:26]1[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59333778HCID 59333778, compoundHCID 178493227HCID 178493227, compound

Product 1

HCID 593337661-(2-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-yl)ethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(3-oxo-3-(4-oxotetrahydro-2H-pyran-3-yl)propyl)pyrrolidin-2-one (202 mg, 0.84 mmol), 1-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)guanidine (1 equiv.) and potassium carbonate (2 equiv.) were heated to 50° C. over night in EtOH (5 mL). The crude product was extracted into DCM and solvent was evaporated. The crude product was purified by flash chromatogaphy (0-100% EtOAc in heptanes) followed by prepHPLC to afford the titled compound.

Workup

  1. extractionThe crude product was extracted into DCM and solvent
  2. customwas evaporated
  3. customThe crude product was purified by flash chromatogaphy (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-0dfd971067b4487081acab2d07b9b480
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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