Hydroxyl phenylboronic acid acid → 4-(8-Amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)phenol

HRID 449074Notes

Reaction equation

HRID 449074 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:20]3[CH2:23][CH2:22][CH2:21]3)=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14](F)=[C:15]([CH:18]=2)C#N)[CH:5]=[CH:6][N:7]=1.[OH:24]OB(C1C=CC=CC=1)O>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH:20]3[CH2:23][CH2:22][CH2:21]3)=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([OH:24])=[CH:15][CH:18]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 58822967Hydroxyl phenylboronic acid acidHCID 669156655-(8-Amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-2-fluorobenzonitrile

Product 1

HCID 1361179304-(8-Amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)phenol

Procedure

Prepared according to a Suzuki coupling procedure analogous to that described for synthesis of 5-(8-amino-3-cyclobutylimidazo[1,5-a]pyrazin-1-yl)-2-fluorobenzonitrile, except using 4 hydroxyphenylboronic acid. MS (ES+): m/z 281.17 (100)[MH+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-36758896728142cabde9b7ce017efe23
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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