Triethylamine → (S)-N-ethyl-2-(3-hydroxypiperidin-1-yl)pyrimidine-5-carboxamide

HRID 59928Notes

Reaction equation

HRID 59928 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[CH:13][C:12]([C:15]([NH:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=1.Cl.[NH:21]1[CH2:26][CH2:25][CH2:24][C@H:23]([OH:27])[CH2:22]1>C(#N)C>[CH2:18]([NH:17][C:15]([C:12]1[CH:11]=[N:10][C:9]([N:21]2[CH2:26][CH2:25][CH2:24][C@H:23]([OH:27])[CH2:22]2)=[N:14][CH:13]=1)=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16211918(3S)-Piperidin-3-ol--hydrogen chloride (1/1)HCID 118366250HCID 118366250, compound

Product 1

HCID 118366212(S)-N-ethyl-2-(3-hydroxypiperidin-1-yl)pyrimidine-5-carboxamideYield 73.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Triethylamine (1.5 mL, 11 mmol) and 2-chloro-N-ethylpyrimidine-5-carboxamide (830 mg, 4.47 mmol) were added sequentially to a solution of (S)-piperidin-3-ol hydrochloride (677 mg, 4.92 mmol) in acetonitrile (25 mL) at 20-25° C. The reaction mixture was heated to 80° C. for 16 hours. The mixture was then cooled to 20-25° C. and was concentrated under reduced pressure. The resulting residue was dissolved in EtOAc (25 mL) and washed with saturated NH4Cl (10 mL) and brine (10 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to provide (S)—N-ethyl-2-(3-hydroxypiperidin-1-yl)pyrimidine-5-carboxamide (827 mg, 73%).

Workup

  1. temperatureThe mixture was then cooled to 20-25° C.
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in EtOAc (25 mL)
  4. washwashed with saturated NH4Cl (10 mL) and brine (10 mL)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d8e0e4332cf940669e87b75322f7dad2
Source dataset
uspto-grants-2016_09
Patent number
US09440949B2

Reaction notes

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