Hydrazine → 7-Pyrimidin-5-yl-1-benzofuran-5-amine

HRID 1161986Notes

Reaction equation

HRID 1161986 reaction equation
NN.[N+:3]([C:6]1[CH:7]=[C:8]([C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)[C:9]2[O:13][CH:12]=[CH:11][C:10]=2[CH:14]=1)([O-])=O>C(O)C.C1COCC1.[Ni]>[N:17]1[CH:16]=[C:15]([C:8]2[C:9]3[O:13][CH:12]=[CH:11][C:10]=3[CH:14]=[C:6]([NH2:3])[CH:7]=2)[CH:20]=[N:19][CH:18]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 66893448HCID 66893448, compound2×

Product 1

HCID 668929957-Pyrimidin-5-yl-1-benzofuran-5-amineYield 80.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Raney-nickel (slurry in ethanol; 2 mL) and hydrazine (0.378 g, 7.55 mmol) were added to 5-(5-nitro-1-benzofuran-7-yl)pyrimidine (0.455 g, 1.87 mmol, Intermediate 17) in ethanol/THF (100 mL:25 mL). The mixture was stirred at room temperature for 3 h, filtered through Celite and concentrated in vacuo to afford 0.317 g (80%) of the title compound as a yellow solid. HPLC 100%, RT: 0.957 min (System A; 10-97% over 3 min). 1H NMR (270 MHz, methanol-d4) δ ppm 6.77 (d, J=2.23 Hz, 1H) 7.05 (q, J=2.23 Hz, 2H) 7.76 (d, J=2.23 Hz, 1H) 9.14 (s, 1H) 9.26 (s, 2H). LC-MS 212 (M+H)+.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e087b75bc424c2e89e2eb4beab9999a
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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