Methyl p-toluenesulfonate → (7S)-2-chloro-8-isopropyl-7-ethyl-5-methyl-7H-pteridin-6-one

HRID 2364766Notes

Reaction equation

HRID 2364766 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C@H:6]([CH2:13][CH3:14])[N:5]([CH:15]([CH3:17])[CH3:16])[C:4]=2[N:3]=1.[C:18]1(C)C=CC(S(OC)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:18])[C:7](=[O:12])[C@H:6]([CH2:13][CH3:14])[N:5]([CH:15]([CH3:16])[CH3:17])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 86668261(7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-one

Product 1

HCID 86668262(7S)-2-chloro-8-isopropyl-7-ethyl-5-methyl-7H-pteridin-6-oneYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The crude compound (7S)-2-chloro-8-isopropyl-7-ethyl-5,7-dihydropteridin-6-one 43c (7.17 g, 28.21 mmol), methyl p-toluenesulfonate (5.77 g, 31.03 mmol) and potassium carbonate (11.70 g, 84.60 mmol) were dissolved in 40 mL of acetone. The reaction solution was stirred for 12 hours and the precipite was filtered. The filter cake was washed with dichloromethane (100 mL). The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system B to obtain (7S)-2-chloro-8-isopropyl-7-ethyl-5-methyl-7H-pteridin-6-one 43d (6.14 g, yield: 81.0%) as a white solid.

Workup

  1. filtrationthe precipite was filtered
  2. washThe filter cake was washed with dichloromethane (100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-71fa6967355f453fb038738493e884bc
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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