Piperidine → 2-Chloro-5-nitro-4-(piperidin-1-yl)pyrimidine

HRID 69837

Reaction equation

HRID 69837 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>CCO>[Cl:1][C:2]1[N:7]=[C:6]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 5212662,4-Dichloro-5-nitropyrimidine

Product 1

HCID 71472572-Chloro-5-nitro-4-(piperidin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Method 1 was followed using 2,4-dichloro-5-nitropyrimidine (1.0 eq), and piperidine (2.0 eq) in EtOH at 0° C. to rt, yielding after washing with 1M citric acid and 1M HCl (to remove the bis addition product), 2-chloro-5-nitro-4-(piperidin-1-yl)pyrimidine (67%) LCMS (m/z): 242.9 (MH+); LC Rt=4.09 min.

Workup

  1. customat 0° C. to rt
  2. customyielding
  3. washafter washing with 1M citric acid and 1M HCl (
  4. customto remove
  5. additionthe bis addition product), 2-chloro-5-nitro-4-(piperidin-1-yl)pyrimidine (67%) LCMS (m/z)

Sources & evidence

ORD record
ord-e8307f40214a44f987c44c5c386c7361
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Linked notes

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