Phosphorus oxychloride → 3-Methyl-8-(5-phenyloxazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one

HRID 570933Notes

Reaction equation

HRID 570933 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12]([NH:14][CH2:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)=[C:5]2[N:4]=[N:3]1.P(Cl)(Cl)(Cl)=O>>[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12]3[O:23][C:16]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:15][N:14]=3)=[C:5]2[N:4]=[N:3]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 668317663-Methyl-4-oxo-N-(2-oxo-2-phenylethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

Product 1

HCID 498707693-Methyl-8-(5-phenyloxazol-2-yl)imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-oneYield 32.2%

Conditions

Temperature
110 °C

Procedure

3-Methyl-4-oxo-N-(2-oxo-2-phenylethyl)-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (0.180 g; 0.58 mmol) was added to phosphorus oxychloride (3.6 mL) and the stirred mixture heated at 110° C. for 1.5 hours. The mixture was cooled and poured onto ice, and allowed to stand for 3 hour. The solid was filtered and extracted with chloroform on Soxhlet apparatus. Concentration under reduced pressure yielded pure title compound as a bright yellow powder (55 mg; 32%). δH (DMSO-d6) 8.94 (1H, s), 7.99 (1H, s), 7.85 (2H, m), 7.55 (2H, m), 7.44 (1H, tt, J=7.8, 1.1), 3.90 (3H, s).

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice
  3. filtrationThe solid was filtered
  4. extractionextracted with chloroform on Soxhlet apparatus
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-9a176b49f33a49a5a80371a4412f3994
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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