4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → HCID 21098075, compound

HRID 1351156Notes

Reaction equation

HRID 1351156 reaction equation
Cl[C:2]1[C:10]2[C:5](=[N:6][C:7]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[N:8][CH:9]=2)[N:4]([CH3:19])[N:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)O1>>[NH2:32][C:31]1[CH:33]=[CH:34][C:28]([C:2]2[C:10]3[C:5](=[N:6][C:7]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[N:8][CH:9]=3)[N:4]([CH3:19])[N:3]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 21098077HCID 21098077, compound

Product 1

HCID 21098075HCID 21098075, compound

Procedure

Prepared as described above in Example 15 starting from N′-(3-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-N,N-diethyl-ethane-1,2-diamine and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline to give the title compound N-[3-(4-amino-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-N′,N′-diethyl-ethane-1,2-diamine; 1H-NMR (MeOH): δ 1.38 (m, 6H), 3.36 (m, 4H), 3.82 (m, 2H), 3.92 (m, 2H), 3.98 (s, 3H), 7.46 (d, 2H, J=8.4 Hz), 8.09 (d, 2H, J=8.4 Hz), 9.18 (s, 1H), LC/MS (m/e)=340.2 (MH+), Rt=0.98 min.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ea6bf968b7d245efb69f12f916450e85
Source dataset
uspto-grants-2007_05
Patent number
US07217710B2

Reaction notes

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