Phosphorus sulfide (P2S5) → HCID 86663781, compound

HRID 570923Notes

Reaction equation

HRID 570923 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14]([NH2:16])=O)=[C:7]2[N:6]=[N:5]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:18].C[Si](C)(C)O[Si](C)(C)C>C(Cl)Cl>[CH3:1][O:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH:11]=[N:12][C:13]([C:14](=[S:18])[NH2:16])=[C:7]2[N:6]=[N:5]1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)2×HCID 24764HexamethyldisiloxaneHCID 15474226HCID 15474226, compound

Product 1

HCID 86663781HCID 86663781, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(Methoxymethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide (0.100 g, 0.446 mmol), phosphorus pentasulfide (27 mg; 0.06 mmol), and hexamethyldisiloxane (87 mg; 0.114 mL; 0.535 mmol) were stirred in DCM under reflux for 24 hours. After 24 hours, a second portion of P2S5 (27 mg; 0.06 mmol) was added, and reflux continued for a further 24 hours, after which time the reaction mixture was filtered, and the precipitate was washed with EtOAc, Et2O and air dried to yield the title compound as an orange solid (67% yield). 1H NMR (400 MHz, d6-DMSO) δ ppm 9.95 (1H, bs), 9.47 (1H, bs), 8.85 (1H, s), 5.74 (2H, s) and 3.40 (3H, s).

Workup

  1. temperatureunder reflux for 24 hours
  2. temperaturereflux
  3. waitcontinued for a further 24 hours
  4. filtrationafter which time the reaction mixture was filtered
  5. washthe precipitate was washed with EtOAc, Et2O and air
  6. customdried

Sources & evidence

ORD record
ord-14b0f51eb308409c911477e67d2fc19c
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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