Methanol → HCID 67255020, compound

HRID 1627741Notes

Reaction equation

HRID 1627741 reaction equation
I[Si](C)(C)C.C[O:7][CH2:8][CH2:9][N:10]1[C:14]([CH2:15][CH2:16][C:17]2[N:27]=[C:20]3[C:21]([CH3:26])=[N:22][CH:23]=[C:24]([CH3:25])[N:19]3[N:18]=2)=[N:13][C:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:11]1.CO.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:25][C:24]1[N:19]2[N:18]=[C:17]([CH2:16][CH2:15][C:14]3[N:10]([CH2:9][CH2:8][OH:7])[N:11]=[C:12]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:13]=3)[N:27]=[C:20]2[C:21]([CH3:26])=[N:22][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24437Sodium SulfiteHCID 85247Trimethylsilyl iodide2×HCID 53251314HCID 53251314, compound

Product 1

HCID 67255020HCID 67255020, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Iodotrimethylsilane (92.0 uL, 0.646 mmol) was added to a stirred solution of 2-{2-[2-(2-Methoxy-ethyl)-5-phenyl-2H-1,2,4-triazol-3-yl]ethyl}-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazine (61 mg, 0.16 mmol) in Chloroform (5 mL) under an atmosphere of Argon at rt. The solution was stirred at rt 4 h. More Iodotrimethylsilane (184 uL, 1.29 mmol) was added and the mixture was stirred at rt ON. MeOH (10 ml) and solid sodium sulfite (0.5 g) was added and the mixture was stirred 30 min, filtered and evaporated. The crude product was purified by silica gel chromatography (Eluent: 0-5% MeOH in EtOAc). Yield: 27 mg (46%) of the title compound as a solid. LC-MS: m/z=364.5 (MH+), tR=1.30 min, Method C.

Workup

  1. stirringthe mixture was stirred at rt ON
  2. stirringthe mixture was stirred 30 min
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by silica gel chromatography (Eluent: 0-5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-97b3a7b03edd4f368d4c3c9fa4c3758d
Source dataset
uspto-grants-2014_07
Patent number
US08785653B2

Reaction notes

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