Ethyl Acetate → 5-chloro-N-(2-(isopropylthio)phenyl)-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine

HRID 2046996Notes

Reaction equation

HRID 2046996 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[CH:21]([S:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27])([CH3:23])[CH3:22].C(OCC)(=O)C>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[S:24][CH:21]([CH3:23])[CH3:22])[C:5]2[N:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 138527202-(Isopropylthio)anilineHCID 582908695,7-dichloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 582908655-chloro-N-(2-(isopropylthio)phenyl)-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5,7-dichloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (0.03 g) and 2-(isopropylthio)aniline (0.1 g) in dioxane (10 mL) was heated at 100° C. for 10 h. It was then cooled down to room temperature and ethyl acetate (20 mL) was added. The mixture was washed with saturated sodium bicarbonate (10 mL), and dried over sodium sulfate. Solvent was removed under reduced pressure and the remaining residue was purified on a silica gel column (ethyl acetate:hexane=1:10) to give desired product. ESMS calculated for C21H21ClN6OS (m/z): 440.1; found (M+H+): 441.1.

Workup

  1. washThe mixture was washed with saturated sodium bicarbonate (10 mL)
  2. dry with materialdried over sodium sulfate
  3. customSolvent was removed under reduced pressure
  4. customthe remaining residue was purified on a silica gel column (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-85a7ec4f5ee44b7eba47caf3c9346bb3
Source dataset
uspto-grants-2013_11
Patent number
US08592432B2

Reaction notes

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