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

HRID 44832

Reaction equation

HRID 44832 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]#[N:8])[N:3]=[CH:2]1.CN[C@@H]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[NH:17][CH3:18].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:25][N:26]([CH:28]=[O:29])[CH3:27]>>[CH:12]1([N:17]2[C:18]3[N:3]=[C:2]([N:1]4[CH:5]=[C:4]([CH2:6][C:7]#[N:8])[N:3]=[CH:2]4)[N:1]=[CH:5][C:25]=3[N:26]([CH3:27])[C:28](=[O:29])[C@H:4]2[CH2:6][CH3:7])[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178510863HCID 178510863, compound

Product 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

Conditions

Temperature
110 °C

Procedure

A mixture of intermediate B (150 mg, 0.509 mmol), 2-(1H-imidazol-4-yl)acetonitrile (1.01 mmol, 2 equivalents, 108 mg), Cut (0.1 equivalents, 0.0509 mmol, 10 mg), trans-1,2 bis(methylamino)cyclohexane (14 mg, 0.102 mmol) and Cs2CO3 (1.01 mmol, 331 mg) in DMF (1 mL) was purged with nitrogen and was subsequently heated in a sealed vial at 110° C. for 18 h. The reaction was diluted with ethyl acetate, filtered through Celite and evaporated. The residue was purified by reverse phase preparative HPLC and lyophilized to give the title compound (185 mg). 1H NMR (CDCl3) δ: 8.66 (s, 1H), 7.91 (s, 1H), 7.76 (s, 1H), 4.31-4.37 (m, 2H), 3.91 (s, 2H), 3.38 (s, 3H), 1.70-2.13 (m, 10H), and 0.93 ppm (t, J=7.4 Hz, 3H); LCMS: 366.1 m/z (M+H)+; ret. Time: 3.444 min (Analytical Method A).

Workup

  1. customwas purged with nitrogen
  2. additionThe reaction was diluted with ethyl acetate
  3. filtrationfiltered through Celite
  4. customevaporated
  5. customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-8cc89f87399b4b3e82cd973d4487ed03
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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