Acetonitrile → 1-(pyrimidin-4-yloxy)-1H-benzo[d][1,2,3]triazole

HRID 932019Notes

Reaction equation

HRID 932019 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([OH:7])=[N:3][CH:2]=1.[N:8]1CCC[N:12]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:13]=12.C(#[N:21])C>>[N:1]1[CH:6]=[CH:5][C:4]([O:7][N:8]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[N:12]=[N:21]2)=[N:3][CH:2]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178516514HCID 178516514, compound

Product 1

HCID 585740071-(pyrimidin-4-yloxy)-1H-benzo[d][1,2,3]triazole

Procedure

To a solution of pyrimidin-4-ol (350 mg, 3.6 mmol) and (1H-benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate(V) (1.9 g, 4.4 mmol) in 24 mL of acetonitrile was added 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (820 μL, 5.5 mmol) dropwise at room temperature. After the reaction mixture was stirred for 1 hour, the reaction solvent was removed under reduced pressure. Purification of the residue by flash chromatography (0 to 70% EtOAc/hexanes) provided the title compound as a light yellow solid.

Workup

  1. customthe reaction solvent was removed under reduced pressure
  2. customPurification of the residue by flash chromatography (0 to 70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d1c831d89cbb4b90ac244797c0402a76
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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