(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile → (R)-2-(4-(2-aminoethyl)-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 2093692

Reaction equation

HRID 2093692 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([CH2:21][C:22]#[N:23])[N:18]=[CH:17]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:24])[C:8](=[O:25])[C@H:7]2[CH2:26][CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.O=[Pt]=O>[NH2:23][CH2:22][CH2:21][C:19]1[N:18]=[CH:17][N:16]([C:13]2[N:12]=[CH:11][C:10]3[N:9]([CH3:24])[C:8](=[O:25])[C@@H:7]([CH2:26][CH3:27])[N:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[C:15]=3[N:14]=2)[CH:20]=1

Participants

4

Reactant 1

HCID 58405740(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile

Product 1

HCID 58405893(R)-2-(4-(2-aminoethyl)-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneYield 42.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile (Example 35, 0.08 g, 0.218 mmol) and PtO2 (40 mg) were suspended in 2 mL of EtOAc and the resulting mixture was stirred under an atmosphere of hydrogen (1 atm, balloon) for 18 h. The resulting solution was filtered through Celite, concentrated, then purified by preparative HPLC to give the title compound (34 mg). LCMS: 370.1 m/z (M+H)+; ret. Time: 4.09 (Analytical Method C).

Workup

  1. filtrationThe resulting solution was filtered through Celite
  2. concentrationconcentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c05fec88cbfb4011ae2184fd967252ed
Source dataset
uspto-grants-2013_05
Patent number
US08445503B2

Linked notes

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