2-Amino-3-Hydroxypyridine → (1,3)Oxazolo(4,5-b)pyridin-2-amine

HRID 1875992Notes

Reaction equation

HRID 1875992 reaction equation
N1([C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[NH:7])C=CN=C1.NC1[C:19]([OH:20])=[CH:18]C=CN=1>C1COCC1>[O:20]1[C:19]2[C:9](=[N:10][CH:11]=[CH:12][CH:18]=2)[N:8]=[C:6]1[NH2:7]

Participants

4

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazole

Product 1

HCID 12730674(1,3)Oxazolo(4,5-b)pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An oven dried round bottom flask was charged with di(1H-imidazol-1-yl)methanimine (500 mg, 3.10 mmol), 2-aminopyridin-3-ol (171 mg, 1.551 mmol) and anhydrous THF (20 ml) at room temperature. The resulting suspension was refluxed under N2 for 1 hr. LC/MS indicated complete consumption of starting material. The solvent was removed in vacuo and the residue was used in the next step without further purification. MS (LC/MS) R.T.=0.235; [M+H]+=136.09.

Workup

  1. customAn oven dried round bottom flask
  2. temperatureThe resulting suspension was refluxed under N2 for 1 hr
  3. customconsumption of starting material
  4. customThe solvent was removed in vacuo
  5. customthe residue was used in the next step without further purification
  6. customMS (LC/MS) R.T.=0.235

Sources & evidence

ORD record
ord-41fb90b30a3745efb1d4e96df70035d9
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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