HCID 86688070, compound → HCID 67469761, compound

HRID 407867Notes

Reaction equation

HRID 407867 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([NH2:15])[CH2:13][CH2:14]2)=[N:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 1

HCID 86688070HCID 86688070, compound

Product 1

HCID 67469761HCID 67469761, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl 1-(5-ethylpyrimidin-2-yl)piperidin-4-ylcarbamate (3.2 g, 10 mmol) in 50% TFA/CH2Cl2 (30 mL) was stirred at ambient temperature for 1 hour. The mixture was concentrated in vacuo. The residue was dissolved in EtOAc (200 mL) and washed with saturated sodium carbonate (200 mL) then brine. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to yield (1-(5-ethylpyrimidin-2-yl)piperidin-4-amine (2.2 g, 11 mmol, 100%). Mass spectrum (apci) m/z=207.1 (M+H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (200 mL)
  3. washwashed with saturated sodium carbonate (200 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86bde3cc5cc14aaf90a814195eba8d57
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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