(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 44839

Reaction equation

HRID 44839 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-375633b2085a4bb3a7a0ebd80fb12d18
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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