N-Iodosuccinimide → (R)-1-(1-(8-cyclobutyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-2-yl)pyrrolidine-2,5-dione

HRID 44856Notes

Reaction equation

HRID 44856 reaction equation
[CH:1]1([N:5]2[C:14]3[N:13]=[C:12]([N:15]4[CH:19]=[CH:18][N:17]=[CH:16]4)[N:11]=[CH:10][C:9]=3[N:8]([CH3:20])[C:7](=[O:21])[C@H:6]2[CH2:22][CH3:23])[CH2:4][CH2:3][CH2:2]1.[CH2:24]1[C:29](=[O:30])[N:28](I)[C:26](=[O:27])[CH2:25]1>C1COCC1>[CH:1]1([N:5]2[C:14]3[N:13]=[C:12]([N:15]4[CH:19]=[CH:18][N:17]=[C:16]4[N:28]4[C:29](=[O:30])[CH2:24][CH2:25][C:26]4=[O:27])[N:11]=[CH:10][C:9]=3[N:8]([CH3:20])[C:7](=[O:21])[C@H:6]2[CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58405613HCID 58405613, compound

Product 1

HCID 58405838(R)-1-(1-(8-cyclobutyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-2-yl)pyrrolidine-2,5-dioneYield 150.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

(R)-8-cyclobutyl-7-ethyl-2-(1H-imidazol-1-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 111, 0.14 g, 0.448 mmol) was dissolved in 2 mL of THF and NIS (0.20 g, 0.896 mmol) was added. The solution was stirred at 80° C. for 6 hours after which the solution was concentrated and purified by preparative HPLC to give the title compound (276 mg). LCMS: 410.2 m/z (M+H)+; ret. Time: 3.81 (Analytical Method A).

Workup

  1. concentrationwas concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-262c0ff802a44ed6995babb6146f6052
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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