Sodium methanethiolate → HCID 18507486, compound

HRID 1355845Notes

Reaction equation

HRID 1355845 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](OS(C(F)(F)F)(=O)=O)[C:5]([N+:16]([O-:18])=[O:17])=[C:4]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:3]=1.[CH3:24][S-:25].[Na+]>O1CCOCC1>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:4]1[C:5]([N+:16]([O-:18])=[O:17])=[C:6]([S:25][CH3:24])[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86583748Trifluoromethanesulfonic acid 2-amino-6-furan-2-yl-5-nitro-pyrimidin-4-yl ester

Product 1

HCID 18507486HCID 18507486, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 335 mg (0.95 mmol) trifluoro-methanesulfonic acid 2-amino-6-furan-2-yl-5-nitro-pyrimidin-4-yl ester and 663 mg (9.46 mmol) sodium methanethiolate in 20 ml dry dioxane under argon was heated at reflux for one hour. The reaction mixture was then concentrated in vacuo. Flash chromatography (ethyl acetate) followed by recrystallisation from ether/hexane afforded 110 mg (46%) 4-furan-2-yl-6-methylsulfanyl-5-nitro-pyrimidin-2-ylamine as a yellow crystalline solid. EI-MS ni/e (%): 252 (M+, 22), 235 (26), 223 (66), 207 (100), 178 (86), 161 (44), 134 (62), 94 (90).

Workup

  1. temperatureat reflux for one hour
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. customFlash chromatography (ethyl acetate) followed by recrystallisation from ether/hexane

Sources & evidence

ORD record
ord-1c855649d7464f60a2df9d0ff172ebf1
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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