3-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → (R)-7-ethyl-8-isopropyl-5-methyl-2-(3-phenylpyridin-4-yl)-7,8-dihydropteridin-6(5H)-one

HRID 44855Notes

Reaction equation

HRID 44855 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]([CH3:18])[CH3:17])[C:4]=2[N:3]=1.[C:19]1([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][C:30]=2B2OC(C)(C)C(C)(C)O2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:14]([C@H:6]1[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]2[N:3]=[C:2]([C:30]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7]1=[O:13])[CH3:15]

Participants

3

Reactant 2

HCID 584053933-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 58405561(R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropyrimido[4,5-b]pyrazine

Product 1

HCID 58405784(R)-7-ethyl-8-isopropyl-5-methyl-2-(3-phenylpyridin-4-yl)-7,8-dihydropteridin-6(5H)-one

Procedure

The title compound was prepared similarly to the methods described in Example 5, with Intermediate C instead of Intermediate B and with 3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Boronic Acid 2) instead of pyridin-4-ylboronic acid. LCMS: 388.2 m/z (M+H)+; ret. Time: 6.56 min (Analytical Method C).

Sources & evidence

ORD record
ord-2f0eb18c0d38409eacd2022a98ffd487
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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