Phosphorus sulfide (P2S5) → HCID 59853799, compound

HRID 249756Notes

Reaction equation

HRID 249756 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([C:15]([F:18])([F:17])[F:16])[NH:11][C:10]=2[C:9](=O)[NH:8][C:7]1=[O:20])[CH2:2][CH2:3][CH2:4][CH3:5].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:22]>O1CCOCC1>[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([C:15]([F:18])([F:17])[F:16])[NH:11][C:10]=2[C:9](=[S:22])[NH:8][C:7]1=[O:20])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 59853804HCID 59853804, compound

Product 1

HCID 59853799HCID 59853799, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-pentyl-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione (0.81 g, 2.8 mmol) and phosphorus pentasulfide (1.2 g, 2.8 mmol) in 1,4-dioxane (20 mL) was heated at 100° C. for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography twice (0-50% MeOH in CH2Cl2) to yield 0.15 g of pure product as a yellow solid (0.15 g, 18% yield). LCMS calculated for C11H14F3N4OS (M+H): 307.1. found: 307.1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography twice (0-50% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f16d5be328ca42cab410ecd8363b5a0e
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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