Methyl iodide → {2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-trimethyl-ammonium iodide

HRID 882910Notes

Reaction equation

HRID 882910 reaction equation
[CH3:1][I:2].[CH3:3][N:4]([CH3:19])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[C:15]([NH2:16])=[N:14][C:13]([NH2:17])=[C:12]([Cl:18])[N:11]=1)=[O:9]>C(Cl)Cl>[I-:2].[NH2:16][C:15]1[C:10]([C:8]([NH:7][CH2:6][CH2:5][N+:4]([CH3:1])([CH3:19])[CH3:3])=[O:9])=[N:11][C:12]([Cl:18])=[C:13]([NH2:17])[N:14]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 151481303,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide2×

Product 1

HCID 57400252{2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-trimethyl-ammonium iodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl iodide (120 μL, 1.9 mmol) is added to a suspension of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (2-dimethylamino-ethyl)-amide (Intermediate H) (100 mg, 0.39 mmol) in DCM (4 mL), and the resultant solution is stirred at RT for 2 h. The white solid which has formed is collected by filtration and washed with DCM (5 mL) to afford the title compound. M+ 273. 1H NMR (400 MHz, DMSO-d6) δ 8.27 (1H, t), 7.09 (2H, br s), 3.61 (2H, m), 3.45 (2H, t), 3.11 (9H, s).

Workup

  1. customThe white solid which has formed
  2. filtrationis collected by filtration
  3. washwashed with DCM (5 mL)

Sources & evidence

ORD record
ord-8a78244253744e2eb3492991cbe6b00c
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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