Triethylamine → 1-(5-Bromopyrimidin-2-yl)piperidin-4-ol

HRID 729458Notes

Reaction equation

HRID 729458 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[NH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]1.C(N(CC)CC)C>CCO>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 46411251-(5-Bromopyrimidin-2-yl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-2-chloropyrimidine (5 g, 25.8 mmol), piperidin-4-ol (2.88 g, 28.4 mmol) and triethylamine (5.40 mL, 38.8 mmol) in EtOH (51.7 mL) was heated at 90° C. for 0.5 h. The solvent was evaporated, the residue was diluted with 1N HCl (20 mL) and extracted with EtOAc (3×15 mL). The combined organic fractions were dried over Na2SO4 and the solvent was evaporated. The product was recrystallized from CH2Cl2/hexanes, filtered and washed with hexanes to afford the title product.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was diluted with 1N HCl (20 mL)
  3. extractionextracted with EtOAc (3×15 mL)
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. customthe solvent was evaporated
  6. customThe product was recrystallized from CH2Cl2/hexanes
  7. filtrationfiltered
  8. washwashed with hexanes

Sources & evidence

ORD record
ord-e75771e8633045fda7a34cfabfbb0348
Source dataset
uspto-grants-2009_09
Patent number
US07582633B2

Reaction notes

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