4-Toluenesulfonyl chloride → HCID 86696633, compound

HRID 1468613Notes

Reaction equation

HRID 1468613 reaction equation
[NH2:1][N:2]1[C:10]2[C:6]([N:7]3[N:13]([CH3:14])[C:12](=[O:15])[N:11]([CH2:16][CH2:17][OH:18])[CH:8]3[N:9]=2)=[C:5]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:4]=[CH:3]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.CCCCCC>N1C=CC=CC=1>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:18][CH2:17][CH2:16][N:11]2[CH:8]3[N:9]=[C:10]4[C:6]([N:7]3[N:13]([CH3:14])[C:12]2=[O:15])=[C:5]([C:19]2[O:20][CH:21]=[CH:22][CH:23]=2)[N:4]=[CH:3][N:2]4[NH2:1])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8058HexaneHCID 66826349HCID 66826349, compound

Product 1

HCID 86696633HCID 86696633, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
26 °C

Procedure

A mixture of 5-amino-8-(2-furyl)-3-(2-hydroxyethyl)-1-methyl-[1,2,4]triazolo[5,1-f]purin-2-one obtained in step 6 (3.5 g, 11 mmol), p-toluene sulphonylchloride (5.2 g, 27 mmol) were taken in pyridine (30 ml) and stirred at 25-27° C. for 16 hours. To the reaction mixture hexane (100 ml) was added and solid obtained was filtered off and washed with water (100 ml) followed by hexane (100 ml) to obtain 2-[5-amino-8-(2-furyl)-1-methyl-2-oxo-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate (4.1 g, 78%) as a brown solid.

Workup

  1. customsolid obtained
  2. filtrationwas filtered off
  3. washwashed with water (100 ml)

Sources & evidence

ORD record
ord-f1807427e03142fe8bca9e4000597602
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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