2-(Tributylstannyl)-1,3-thiazole → (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(thiazol-2-yl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

HRID 44843

Reaction equation

HRID 44843 reaction equation
Br[C:2]1[N:3]([C:7]2[N:16]=[CH:15][C:14]3[N:13]([CH3:17])[C:12](=[O:18])[C@@H:11]([CH2:19][CH3:20])[N:10]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[C:9]=3[N:8]=2)[CH:4]=[CH:5][N:6]=1.C([Sn](CCCC)(CCCC)[C:31]1[S:32][CH:33]=[CH:34][N:35]=1)CCC>>[CH:21]1([N:10]2[C:9]3[N:8]=[C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[C:31]4[S:32][CH:33]=[CH:34][N:35]=4)[N:16]=[CH:15][C:14]=3[N:13]([CH3:17])[C:12](=[O:18])[C@H:11]2[CH2:19][CH3:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 58405307(R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

Product 1

HCID 58405426(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(2-(thiazol-2-yl)-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

Procedure

The title compound was prepared similarly to the methods described in Example 54, with (R)-2-(2-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 65) used instead of (R)-2-(4-bromo-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 43) and with 2-(tributylstannyl)thiazole instead of 4-(tributylstannyl)thiazole. LCMS: 410.1 m/z (M+H)+; ret. Time: 3.11 min (Analytical Method A).

Sources & evidence

ORD record
ord-666a5a2a967d4c9f98a6f91d88a29949
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Linked notes

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