Carbon Disulfide → 9-pentyl-3-thioxo-2,3,6,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 2368558Notes

Reaction equation

HRID 2368558 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8]/[C:7]/1=[N:16]\[NH2:17])[CH2:2][CH2:3][CH2:4][CH3:5].[C:18](=S)=[S:19]>N1C=CC=CC=1>[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[N:8]2[C:18](=[S:19])[NH:17][N:16]=[C:7]12)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6348Carbon DisulfideHCID 178446164HCID 178446164, compound

Product 1

HCID 576002849-pentyl-3-thioxo-2,3,6,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 84.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (2e)-3-pentyl-3,7-dihydro-1h-purine-2,6-dione 2-hydrazone (1.90 g, 8.04 mmol) and carbon disulfide (0.58 ml, 9.64 mmol) in pyridine (30 ml) was stirred at 60° C. for 3 hours. After cooling to room temperature, the solid formed was filtered and dried to yield the desired product (1.90 g, 84.9%). LCMS calculated for: C11H14N6OS (M+H) 280.1. Found: 280.1.

Workup

  1. customthe solid formed
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-35546d283bb3414d83759095838f0368
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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