Methyl iodide → HCID 178491347, compound

HRID 929664Notes

Reaction equation

HRID 929664 reaction equation
CI.[Br:3][C:4]1[N:9]=[C:8]([NH:10][C:11]([NH2:13])=S)[CH:7]=[CH:6][CH:5]=1.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:17]=1[CH2:18][NH2:19]>CO.C(O)C>[Br:3][C:4]1[N:9]=[C:8]([NH:10][C:11]([NH:19][CH2:18][C:17]2[C:20]([O:24][CH3:25])=[CH:21][CH:22]=[CH:23][C:16]=2[O:15][CH3:14])=[NH:13])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 28008722,6-DimethoxybenzylamineHCID 22170428(6-Bromo-pyridin-2-YL)thiourea

Product 1

HCID 178491347HCID 178491347, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

0.37 mL (5.89 mmol) methyl iodide diluted in 2 mL methanol was added dropwise to 1.032 g (4.46 mmol) N-(6-bromopyridin-2-yl)thiourea suspended in 30 mL methanol, and the mixture was heated for 2 hr under reflux. The reaction mixture was in solution. The methylated intermediate product, consisting of methyl N-(6-bromopyridin-2-yl)imidothiocarbamate hydroiodide (ESI-MS [M+H+]=247.85 calculated for C7H8BrN3S=246), was freed of solvent under vacuum. The intermediate product was then suspended in 30 mL ethanol, and 1.122 g (6.442 mmol) 2,6-dimethoxybenzylamine was added, whereupon the solid completely dissolved. The mixture was then heated for 2.25 hr under reflux. The colorless solid which precipitated was suctioned off and washed with ethanol. 1.197 g N-(6-bromopyridin-2-yl)-N′-(2,6-dimethoxybenzyl)guanidine was obtained as crude product. Repeated crystallization from acetonitrile/water resulted in the isolation of 1.311 g (3.589 mmol, 81%) N-(6-bromopyridin-2-yl)-N-(2,6-dimethoxybenzyl)guanidine, which was also used for the subsequent reaction and derivatizations.

Workup

  1. temperaturethe mixture was heated for 2 hr
  2. temperatureunder reflux
  3. dissolutioncompletely dissolved
  4. temperatureThe mixture was then heated for 2.25 hr
  5. temperatureunder reflux
  6. customThe colorless solid which precipitated
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-54dc2377270a479ba0b8d70fdf47945d
Source dataset
uspto-grants-2016_03
Patent number
US09296697B2

Reaction notes

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