Pyrazol-3-ylamine → 6-Chloro-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthalene

HRID 883833Notes

Reaction equation

HRID 883833 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[NH2:11][C:12]1[NH:16][N:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>C1COCC1>[Cl:10][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[C:7]=1[CH:8]=[N:11][C:12]1[N:16]2[N:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 74561Pyrazol-3-ylamineHCID 81531DiisopropylethylamineHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 866548856-Chloro-1,4,7,9,9b-pentaaza-cyclopenta[a]naphthaleneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 1a (1.24 g, 7.01 mmol) in 30 mL of THF was reacted with 5-aminopyrazole (0.58 g, 7.01 mmol) in 10 mL of THF under an argon atmosphere by dropwise addition. The mixture was stirred at room temperature for 1 hour and then added diisopropylethylamine (1.22 mL, 7.01 mmol) dropwise with stirring. The mixture was heated overnight at 60° C., and quenched with water and extracted with EtOAc, washed with brine, and dried over Na2SO4. The product was filtered and the solvent was removed under vacuum. The product was purified by silica gel chromatography eluting with EtOAc/hexane to give the title compound as a pale yellow solid (405 mg, 29%).

Workup

  1. temperatureThe mixture was heated overnight at 60° C.
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe product was filtered
  7. customthe solvent was removed under vacuum
  8. customThe product was purified by silica gel chromatography
  9. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-38af4f81b0a0495e889ba97df1a39923
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

Loading…