3-Methylbenzaldehyde → HCID 58178996, compound

HRID 1042018Notes

Reaction equation

HRID 1042018 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH2:7].[CH3:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.[N+:17]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)#[C-:18]>CO.O=[Pt]=O>[C:9]1([CH3:8])[CH:16]=[CH:15][CH:14]=[C:11]([C:12]2[N:7]=[C:2]3[CH2:3][NH:4][CH2:5][CH2:6][N:1]3[C:18]=2[NH:17][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 121053-MethylbenzaldehydeHCID 235621-Isocyano-4-methylbenzeneHCID 78747Aminopyrazine

Product 1

HCID 58178996HCID 58178996, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent2×

Procedure

Example 266 was synthesized by the following way: to a 100-mL round-bottom flask, was placed a solution of pyrazin-2-amine (1.2 g, 12.6 mmol), 3-methylbenzaldehyde (1.44 g, 12.0 mmol) and HClO4 (200 mg, 2.0 mmol) in methanol (10 mL). The reaction mixture was stirred at room temperature for 30 minutes, then to the mixture was added 1-isocyano-4-methylbenzene (1.2 g, 10.3 mmol). The resulting solution was allowed to stir for 12 hr at room temperature. After removing the solvent, the residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to result 1.1 g the Ugi adduct. To a solution of the obtained Ugi adduct (1.0 g, 3.18 mmol) in methanol (50 mL) was added PtO2 (72 mg, 0.32 mmol). Then the reaction mixture was evacuated and back filled with H2. The reaction mixture was stirred at RT overnight. The solid was filtered out and the filtrate was concentrated under vacuum to result in the title compound as a white solid.

Workup

  1. customExample 266 was synthesized by the following way
  2. customto a 100-mL round-bottom flask, was placed
  3. stirringto stir for 12 hr at room temperature
  4. customAfter removing the solvent
  5. customto result 1.1 g the Ugi adduct
  6. customThen the reaction mixture was evacuated
  7. additionback filled with H2
  8. stirringThe reaction mixture was stirred at RT overnight
  9. filtrationThe solid was filtered out
  10. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-dd2805243bad43f798966b0bfdae76d4
Source dataset
uspto-grants-2013_10
Patent number
US08557801B2

Reaction notes

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