Methyl iodide → 2-(Methylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1261919Notes

Reaction equation

HRID 1261919 reaction equation
[S:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]2=[CH:9][CH:10]=[CH:11][N:4]2[NH:3]1.[CH3:12]I>O1CCCC1>[CH3:12][S:1][C:2]1[NH:7][C:6](=[O:8])[C:5]2=[CH:9][CH:10]=[CH:11][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 574160482-thioxo-1H-pyrrolo[2,1-f][1,2,4]triazin-4-one

Product 1

HCID 1357420592-(Methylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a Round bottom flask, 2-Thioxo-2,3-dihydro-1H-pyrrolo[2,1-f][1,2,4]triazin-4-one (29.22 g, 0.1748 mol), Tetrahydrofuran (800 mL) and Methyl iodide (14.0 mL, 0.225 mol) were added, respectively. The reaction was stirred at room temperature overnight. The solvent was removed under vacuum to give a solid. The combined solid was washed 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 2-Methylsulfanyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one as a white solid which was allowed to dry under vacuum overnight, affording 23.23 grams. 1H NMR (400 MHz, DMSO, d6) δ 12.02 (s, 1H), 7.52 (m, 1H), 6.84 (m, 1H), 6.47 (m, 1H), 2.53 (s, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. customto give a solid
  3. washThe combined solid was washed with water (500 mL) and saturated NaHCO3 (500 mL)
  4. stirringThe mixture was stirred for 30 minutes
  5. filtrationThe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-691bdb0e86f44a57a082a395d4449860
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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