Hydrazine hydrate (1:1) → HCID 58382089, compound

HRID 1628069Notes

Reaction equation

HRID 1628069 reaction equation
[NH:1]([C:3]1[N:4]=[C:5]2[C:11]([CH3:12])=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([CH3:24])[O:23][CH2:22][CH2:21][O:20]4)=[CH:15][CH:14]=3)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:6]2=[N:7][CH:8]=1)[NH2:2].O.NN.[CH:36](OCC)(OCC)OCC>>[CH3:12][C:11]1[C:5]2[N:4]3[CH:36]=[N:2][N:1]=[C:3]3[CH:8]=[N:7][C:6]=2[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[C:10]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([CH3:24])[O:20][CH2:21][CH2:22][O:23]2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 31214Ethyl orthoformateHCID 67361565HCID 67361565, compound

Product 1

HCID 58382089HCID 58382089, compoundYield 60%

Conditions

Temperature
100 °C

Procedure

To a flask was added 2-hydrazinyl-7-methyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.357 g, 0.784 mmol, prepared using O from Preparation #20 with hydrazine hydrate) in triethyl orthoformate (3.91 mL, 23.5 mmol). The mixture was heated to about 100° C. for about 20 h. The mixture was concentrated in vacuo to give a residue. The residue was loaded directly on a silica gel column and eluted with 0 to 8% MeOH/DCM to provide 8-methyl-7-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.220 g, 60%): LC/MS (Table 2, Method g) Rt=1.66 min; MS m/z 466 (M+H)+.

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a residue
  4. washeluted with 0 to 8% MeOH/DCM

Sources & evidence

ORD record
ord-69ad0414b8344f7b8b61265c112d6311
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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