Isoamyl Nitrite → HCID 9857266, compound

HRID 750508Notes

Reaction equation

HRID 750508 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[C:10]([NH2:12])[N:9]=[C:8]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:7]=1[N+:21]([O-])=O.[N:24](OCCC(C)C)=O>CCO.CCOC(C)=O.[Pd]>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[N:21]=[N:24][N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:8]=2[N:9]=[C:10]([NH2:12])[N:11]=1

Participants

6

Reactant 2

HCID 8053Isoamyl NitriteHCID 25186553HCID 25186553, compound

Product 1

HCID 9857266HCID 9857266, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 6-(2-furyl)-5-nitro-N4-(2-pyridylmethyl)pyrimidine-2,4-diamine (270 mg, 0.864 mmol) and 10% Pd/C (92 mg, 0.086 mmol) in EtOH (30 mL) and EtOAc (10 mL) was stirred under an hydrogen atmosphere for 1 h, filtered through Celite and concentrated in vacuo. The resulting yellow oil was dissolved in dioxane (25 mL), treated with isoamyl nitrite (0.109 mL, 0.815 mmol), stirred at 100° C. for 6 h, cooled to room temperature, filtered through Celite, concentrated in vacuo and triturated with Et2O to give the title compound (110 mg, 46%) as a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting yellow oil was dissolved in dioxane (25 mL)
  4. temperaturecooled to room temperature
  5. filtrationfiltered through Celite
  6. concentrationconcentrated in vacuo
  7. customtriturated with Et2O

Sources & evidence

ORD record
ord-375eb8515b7744729b32160185391d0c
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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