Methyl iodide → N-(2,6-dimethoxybenzyl)-N'-(5-iodopyridin-2-yl)guanidine

HRID 929655Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

2.019 g (7.233 mmol) N-(5-iodopyridin-2-yl)thiourea was dissolved in 50 mL methanol, 0.60 mL (9.553 mmol) methyl iodide in 2 mL methanol was added dropwise, and the mixture was heated for 2.7 hr at 75° C. (oil bath temperature). The solvent was removed under vacuum, and the intermediate product was redissolved in 50 mL ethanol. 1.870 g (0.736 mmol) 2,6-dimethoxybenzylamine was added to the reaction mixture and heated for 2.25 hr at 90° C. (oil bath temperature). The solvent was then evaporated under vacuum. The crude product was dissolved in acetonitrile, and the product crystallized out with addition of water. The solid was suctioned off and washed with water. 2.698 g (6.152 mmol, 85%) N-(2,6-dimethoxybenzyl)-N′-(5-iodopyridin-2-yl)guanidine was isolated and used for further reaction.

Workup

customThe solvent was removed under vacuum
dissolutionthe intermediate product was redissolved in 50 mL ethanol
temperatureheated for 2.25 hr at 90° C. (oil bath temperature)
customThe solvent was then evaporated under vacuum
dissolutionThe crude product was dissolved in acetonitrile
customthe product crystallized out with addition of water
washwashed with water

Sources & evidence

ORD record: ord-eba051d85d0b4594acd6f3b757511359
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296697B2

Reaction notes

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