Acetaldehyde → HCID 58382478, compound

HRID 1628068Notes

Reaction equation

HRID 1628068 reaction equation
[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[C:10]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[N:9]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:6]2=[N:7][CH:8]=1)[NH2:2].[CH:26](=O)[CH3:27]>C(Cl)Cl.CN(C=O)C.[Cu](Cl)Cl>[CH3:26][C:27]1[N:4]2[C:5]3[CH:11]=[C:10]([C:12]4[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=4)[N:9]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:6]=3[N:7]=[CH:8][C:3]2=[N:1][N:2]=1

Participants

6

Reactant 2

HCID 177AcetaldehydeHCID 58382051HCID 58382051, compound

Product 1

HCID 58382478HCID 58382478, compoundYield 37.5%

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask was added 2-hydrazinyl-6-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.100 g, 0.278 mmol, Preparation #P.2.1) and acetaldehyde (0.079 mL, 1.3 mmol) in DCM (3 mL). The mixture was stirred at rt for about 90 min. The mixture was concentrated in vacuo to give a residue. The residue was transferred to a flask and copper(II) chloride (0.075 g, 0.56 mmol) in DMF (3 mL) was added. The mixture was heated to about 90° C. for about 2 h. The mixture was cooled to rt, diluted with ice water (50 mL) and the solid was collected by filtration. The solid was taken up in DCM/MeOH and the insoluble solids were collected by filtration while the mother liquor was purified by flash chromatography (25 g silica gel column, DCM/EtOAc/MeOH 1:0:0 to 0:1:0 to 9:0:1) to give a solid. The solids were combined to give 1-methyl-7-(1-methyl-1H-pyrazol-4-yl)-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.04 g, 37%): LC/MS (Table 2, Method c) Rt=1.48 min; MS m/z 384 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue
  3. customThe residue was transferred to a flask
  4. temperatureThe mixture was heated to about 90° C. for about 2 h
  5. temperatureThe mixture was cooled to rt
  6. filtrationthe solid was collected by filtration
  7. filtrationthe insoluble solids were collected by filtration while the mother liquor
  8. customwas purified by flash chromatography (25 g silica gel column, DCM/EtOAc/MeOH 1:0:0 to 0:1:0 to 9:0:1)
  9. customto give a solid

Sources & evidence

ORD record
ord-ecb24d4b2afa41cdb3ec4621e81c3571
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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