Piperidine → 4-Chloro-6-piperidin-1-yl-pyrimidin-2-ylamine

HRID 2367186Notes

Reaction equation

HRID 2367186 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CO>[Cl:8][C:6]1[CH:7]=[C:2]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=[C:4]([NH2:9])[N:5]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 14842894-Chloro-6-piperidin-1-yl-pyrimidin-2-ylamineYield 87.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

In a 25 mL sealable tube under argon were combined 4,6-dichloro-2-pyrimidinamine (0.50 g, 3.05 mmol), piperidine (0.75 mL, 7.62 mmol) and CH3OH (10 mL). The vial was sealed and the reaction mixture was stirred for 4 hours at 50° C. The reaction was cooled to room temperature and concentrated. The resulting solid was partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and concentrated to afford the title compound (565 mg, 83%) as a yellow solid. LC-MS (ES) m/z=213 [M+H]+.

Workup

  1. customIn a 25 mL sealable tube under argon were combined
  2. customThe vial was sealed
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated
  5. customThe resulting solid was partitioned between EtOAc and water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ae3399166fa844c49e2217439bd0d27c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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