5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-1,3-benzodioxole → 6-(Benzo[d][1,3]dioxol-5-yl)-n-(3-methoxyphenyl)-1-methyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876919Notes

Reaction equation

HRID 876919 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:11])[N:9]=[CH:10][C:5]2=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[N:3]=1.[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][C:23]=2[O:22]1>>[O:22]1[C:23]2[CH:24]=[CH:25][C:26]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([NH:12][C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=4)[N:3]=3)=[CH:27][C:28]=2[O:29][CH2:21]1

Participants

3

Reactant 2

HCID 27605895-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-1,3-benzodioxoleHCID 46261794HCID 46261794, compound

Product 1

HCID 441815906-(Benzo[d][1,3]dioxol-5-yl)-n-(3-methoxyphenyl)-1-methyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with 3,4-methylenedioxyphenylboronic acid pinacol ester using General Procedure A. Purification on silica yielded 119. NMR: (CDCl3): 3.88 (s, 3H, CH3), 4.10 (s, 3H, CH3), 6.07 (s, 2H, CH2), 6.86 (dd, H, ArH, J=1.81, 8.3), 6.93 (d, H, ArH, J=8.2), 7.13 (m, 2H, 2×ArH), 7.33 (s, H, NH), 7.38 (t, H, ArH, J=8.11), 7.47 (s, H, ArH), 8.06 (d, H, ArH, J=1.54), 8.17 (dd, H, ArH, J=1.63, 8.21). MS: (ESI+) MH+=376.18

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-ce1be6f035544f7fbb6fb1865f55cad6
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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