(Pyridin-4-yl)boronic acid → (R)-7-ethyl-5-methyl-8-(1-methyl-1H-pyrazol-3-yl)-2-(2-phenylpyridin-3-yl)-7,8-dihydropteridin-6(5H)-one

HRID 44898Notes

Reaction equation

HRID 44898 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]CC3)[C:4]=2[N:3]=1.[C:21]1([C:27]2[C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(C2C=[N:50][CH:51]=CC=2B2OC(C)(C)C(C)(C)O2)C=CC=CC=1.[N:63]1C=CC(B(O)O)=CC=1>>[CH2:14]([C@H:6]1[N:5]([C:16]2[CH:20]=[CH:19][N:50]([CH3:51])[N:63]=2)[C:4]2[N:3]=[C:2]([C:32]3[C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:28][CH:29]=[CH:30][CH:31]=3)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7]1=[O:13])[CH3:15]

Participants

5

Reactant 4

HCID 2734379(Pyridin-4-yl)boronic acidHCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneHCID 584053933-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 671220292-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

Product 1

HCID 53261910(R)-7-ethyl-5-methyl-8-(1-methyl-1H-pyrazol-3-yl)-2-(2-phenylpyridin-3-yl)-7,8-dihydropteridin-6(5H)-one

Procedure

The title compound is prepared similarly to the methods described in Example 5, with Intermediate QQ-2 instead of Intermediate B and with 2-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (prepared similarly to the methods used for Boronic Acid 2) instead of pyridin-4-ylboronic acid.

Workup

  1. customprepared similarly to the methods

Sources & evidence

ORD record
ord-8e210ef2f4a744a19abe035939150f73
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

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