Methyl iodide → 2-[1-(1-Methylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-l-yl]pyrimidine

HRID 2268960Notes

Reaction equation

HRID 2268960 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1.I[CH3:26]>CCO>[CH3:26][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH2:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 183326302-[1-(Piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine

Product 1

HCID 207120082-[1-(1-Methylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-l-yl]pyrimidineYield 18.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[1-(piperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (EXAMPLE 18) (20.9 mg, 0.065 mmol) in EtOH (0.6 mL) was added iodomethane (40 μL, 0.65 mmol). The mixture was placed in an oil bath at 60° C. and heated for 4 h, then stirred at room temperature overnight. The solvent was removed under reduced pressure, and the crude product was purified by preparative thin layer chromatography (1:9 2M NH3 in MeOH:CH2Cl2) to obtain 4.1 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.35 (br s, 1H); 8.16 (d, J=7.5 Hz, 1H); 7.84 (d, J=7.1 Hz, 1H); 7.37 (m, 2H); 6.75 (d, J=5.5 Hz, 1H); 4.12 (m, 1H); 2.92 (d, J=9 Hz, 1H); 2.8 (d, J=11 Hz, 1H); 2.27 (s, 3H); 1.26 (d, J=6.7 Hz, 3H). Mass spectrum 337.3 (ESI, M+1).

Workup

  1. customThe mixture was placed in an oil bath at 60° C.
  2. temperatureheated for 4 h
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product was purified by preparative thin layer chromatography (1:9 2M NH3 in MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-502c5eba877341e699fefe6a8514d332
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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