Phosphorus sulfide (P2S5) → HCID 86663780, compound

HRID 570922Notes

Reaction equation

HRID 570922 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH3:15][S:16][CH2:17][N:18]1[C:23](=[O:24])[N:22]2[CH:25]=[N:26][C:27]([C:28]([NH2:30])=O)=[C:21]2[N:20]=[N:19]1.C[Si](C)(C)O[Si](C)(C)C>C(Cl)Cl>[CH3:15][S:16][CH2:17][N:18]1[C:23](=[O:24])[N:22]2[CH:25]=[N:26][C:27]([C:28](=[S:2])[NH2:30])=[C:21]2[N:20]=[N:19]1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 24764HexamethyldisiloxaneHCID 44128652HCID 44128652, compound

Product 1

HCID 86663780HCID 86663780, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus pentasulfide (25 mg, 0.11 mmol) was added in one portion to a suspension of 3-(methylthiomethyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide and hexamethyldisiloxane (85 mg; 0.112 mL, 0.525 mmol) in DCM (5 mL) and the mixture was refluxed overnight. The crude product was absorbed on silica and purified by flash chromatography using DCM:MeOH (95:5) as eluent to give 39 mg of the title compound as an orange solid (36% yield). δH (DMSO d6): 9.95 (1H, s), 9.47 (1H, s), 8.85 (1H, s), 5.43 (2H, s), 2.26 (3H, s).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. customThe crude product was absorbed on silica
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-78d3cd0ccb504150affec2dcde3669ff
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Reaction notes

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