Piperidine → 2-[1-(5-Methoxy-3-piperidin-1-yl-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine

HRID 1609854Notes

Reaction equation

HRID 1609854 reaction equation
Cl[C:2]1[C:3]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:4][CH:5]=[C:6]([O:8][CH3:9])[N:7]=1.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:9][O:8][C:6]1[N:7]=[C:2]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:3]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:4][CH:5]=1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 103575922-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine

Product 1

HCID 102473812-[1-(5-Methoxy-3-piperidin-1-yl-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine

Conditions

Temperature
110 °C

Procedure

A mixture of 2-[1-(3-chloro-5-methoxy-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine (30 mg, 0.099 mmol), and piperidine (1 mL) is heated at 110° C. in a sealed tube for 1 hour. On cooling, the volatile materials are removed in vacuo and the residue is purified by PTLC (silica gel; 10% MeOH in DCM) to give 35 mg of 2-[1-(5-Methoxy-3-piperidin-1-yl-pyrazin-2-ylmethyl)-1H-imidazol-2-yl]-pyrimidine. 1H NMR (CDCl3) 8.74 (d, 2H), 7.62 (s, 1H), 7.21 s, 1H), 7.08–7.15 (m, 2H), 5.86 (s, 2H), 3.87 (s, 3H), 3.06–3.15 (m, 4H), 1.52–1.66 (m, 6H).

Workup

  1. temperatureOn cooling
  2. customthe volatile materials are removed in vacuo
  3. customthe residue is purified by PTLC (silica gel; 10% MeOH in DCM)

Sources & evidence

ORD record
ord-e615be6038e64aafaadb252d181f0ce0
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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