Dimethyl Sulfate → 3-(methylthio)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 1664516Notes

Reaction equation

HRID 1664516 reaction equation
[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:16](=[S:19])[NH:17][N:18]=[C:7]12)[CH2:2][CH2:3][CH2:4][CH3:5].S(OC)(O[CH3:24])(=O)=O.[OH-].[Na+]>O>[CH3:24][S:19][C:16]1[N:8]2[C:9](=[O:15])[C:10]3[NH:11][CH:12]=[N:13][C:14]=3[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]2=[N:18][N:17]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 576002849-pentyl-3-thioxo-2,3,6,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one

Product 1

HCID 576003133-(methylthio)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-oneYield 85.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 9-pentyl-3-thioxo-2,3,6,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (1.90 g, 6.83 mmol), dimethyl sulfate (1.03 g, 8.19 mmol) and 1 M of sodium hydroxide in water (25 ml) was stirred at room temperature for 1 hour. The mixture was neutralized to pH=7. The solid formed was filtered and dried to provide the desired product (1.70 g, 85.2%). 1HNMR (300 MHz, CD3OD): δ 4.29 (t, J=7.2 Hz, 2H), 2.65 (s, 3H), 1.89 (m, 2H), 1.40 (m, 4H), 0.92 (m, 3H). LCMS calculated for: C12H17N6OS (M+H) 294.1. found: 294.1.

Workup

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

Sources & evidence

ORD record
ord-f7be218ec6a94d47a12868a6082ac9c6
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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