5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 5-(4-(3-Methoxyphenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidin-6-yl)pyridin-2-amine

HRID 876925Notes

Reaction equation

HRID 876925 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[N:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=1>>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:12][C:4]1[N:3]=[C:2]([C:25]2[CH:26]=[CH:27][C:22]([NH2:21])=[N:23][CH:24]=2)[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]=12

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 583459596-Chloro-4-(3-methoxy-phenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 441817105-(4-(3-Methoxyphenoxy)-1-methyl-1h-pyrazolo[3,4-d]pyrimidin-6-yl)pyridin-2-amine

Procedure

6-Chloro-4-(3-methoxy-phenoxy)-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (80 mg) was coupled to 2-aminopyridine-5-boronic acid pinacol ester via General Procedure A. The product was purified by reverse phase HPLC to yield 47.3 mg of 125. MS (Q1) 349.2 (M)+

Workup

  1. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-4448b6d8d95d4673bf093407524ee417
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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