Methyl iodide → 6-Bromo-2-methylsulfanyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

HRID 1262278Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[NH:8][C:7](=[S:11])[NH:6][C:5]2=[O:12].[CH3:13]I>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[C:7]([S:11][CH3:13])[NH:6][C:5]2=[O:12]

Participants

Conditions

Temperature: 45 °C

Procedure

Into a round bottom flask, 6-Bromo-2-thioxo-2,3-dihydro-1H-pyrrolo[2,1-f][1,2,4]triazin-4-one (11.20 g, 0.04551 mol), Tetrahydrofuran (200 mL) and Methyl iodide (6.517 mL, 0.1047 mol) were added, respectively. The reaction was stirred at 45° C. for one hour. The solid was filtered. The solvent was removed under vacuum to give a solid. The combined solid was partitioned with water (500 mL) and saturated NaHCO3 (500 mL). The mixture was stirred for 30 minutes. The solid was filtered and washed with water to give 6-Bromo-2-methylsulfanyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as a white solid (5.80, 49%).

Workup

filtrationThe solid was filtered
customThe solvent was removed under vacuum
customto give a solid
customThe combined solid was partitioned with water (500 mL) and saturated NaHCO3 (500 mL)
stirringThe mixture was stirred for 30 minutes
filtrationThe solid was filtered
washwashed with water

Sources & evidence

ORD record: ord-c784874467094115b86f8cc95e451658
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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