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

HRID 44831Notes

Reaction equation

HRID 44831 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.[NH:19]1[CH:23]=[C:22](B(O)O)[CH:21]=[N:20]1>>[CH2:14]([C@H:6]1[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]2[N:3]=[C:2]([C:22]3[CH:23]=[N:19][NH:20][CH:21]=3)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7]1=[O:13])[CH3:15]

Participants

3

Reactant 2

HCID 177502781H-Pyrazole-4-boronic acidHCID 58405561(R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropyrimido[4,5-b]pyrazine

Product 1

HCID 58405749(R)-7-ethyl-8-isopropyl-5-methyl-2-(1H-pyrazol-4-yl)-7,8-dihydropteridin-6(5H)-one

Procedure

The title compound was prepared similarly to the methods described in Example 5, using Intermediate C instead of Intermediate B and pyrazol-4-ylboronic acid instead of pyridin-4-ylboronic acid. 1H NMR (CDCl3) δ: 8.23 (broad, 2H), 7.85 (s, 1H), 4.63 (m, 1H), 4.33 (m, 1H), 3.36 (s, 3H), 1.95 (m, 1H), 1.75 (m, 1H), 1.44 (dd, 6H) and 0.87 ppm (t, 3H); LCMS: 301.2 m/z (M+H)+; ret. Time: 1.30 min (Analytical Method E).

Sources & evidence

ORD record
ord-47e6d7bd56554f248bcd057180357eae
Source dataset
uspto-grants-2013_09
Patent number
US08541418B2

Reaction notes

Loading…