Potassium Carbonate → HCID 59625260, compound

HRID 2192835Notes

Reaction equation

HRID 2192835 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH2:36][CH:37]([CH3:39])[CH3:38])[CH:21]2[CH2:26][CH:25]([CH2:27][OH:28])[CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]2)=[O:19])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)[C:8]([C:18]([N:20]([CH:21]2[CH2:26][CH:25]([CH2:27][OH:28])[CH2:24][NH:23][CH2:22]2)[CH2:36][CH:37]([CH3:39])[CH3:38])=[O:19])=[CH:7][N:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59625636HCID 59625636, compound

Product 1

HCID 59625260HCID 59625260, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-[({2-tert-butyl-4-[(furan-2-ylmethyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-(hydroxymethyl)piperidine-1-carboxylate (50.0 mg) was dissolved in trifluoroacetic acid (50% 1,2-dichloroethane solution, 4 ml), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was basified with saturated aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane-methanol (50:50:0-100:0:0-85:0:15) was concentrated under reduced pressure to give the object compound (24.4 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe fraction eluted with ethyl acetate-hexane-methanol (50:50:0-100:0:0-85:0:15)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-886c5c89bdfa449a8c4e480576b38e88
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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