2-cyclopropyl-1H-imidazole → (R)-8-cyclopentyl-2-(2-cyclopropyl-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 44889

Reaction equation

HRID 44889 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:4]=2[N:3]=1.[CH:21]1([C:24]2[NH:25][CH:26]=[CH:27][N:28]=2)[CH2:23][CH2:22]1>[Pd]>[CH:16]1([N:5]2[C:4]3[N:3]=[C:2]([N:25]4[CH:26]=[CH:27][N:28]=[C:24]4[CH:21]4[CH2:23][CH2:22]4)[N:11]=[CH:10][C:9]=3[N:8]([CH3:12])[C:7](=[O:13])[C@H:6]2[CH2:14][CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 179423832-cyclopropyl-1H-imidazoleHCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Product 1

HCID 58405469(R)-8-cyclopentyl-2-(2-cyclopropyl-1H-imidazol-1-yl)-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Intermediate B was reacted via palladium coupling with 2-cyclopropyl-1H-imidazole (synthesized according to U.S. Pat. No. 6,610,723, column 91, Example 409, the disclosure of which is hereby incorporated by reference with respect to this compound) to provide the title compound. 1H NMR (CD3OD) δ: 8.05 (s, 1H), 8.04 (d, J=2.2 Hz, 1H), 7.46 (d, J=2.2 Hz, 1H), 4.43 (pent, J=3.7 Hz, 2H), 3.40 (s, 3H), 3.21 (pent, J=3.3 Hz, 1H), 2.20-2.05 (m, 1H), 2.05-1.77 (m, 7H), 1.75-1.60 (m, 2H), 1.36 (d, J=7.5 Hz, 2H), 1.30-1.10 (m, 2H), 0.87 (t, J=7.5 Hz, 3H); LCMS: 367.1 m/z (M+H)+; ret. Time: 6.70 min (Analytical Method C).

Workup

  1. customsynthesized

Sources & evidence

ORD record
ord-12623be93dd243adbe73b39f5553d9ee
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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