4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole → 2-(1H-indazol-4-yl)-6-((1-methylpiperidin-4-ylidene)methyl)-4-morpholinothieno[3,2-d]pyrimidine

HRID 2262105Notes

Reaction equation

HRID 2262105 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:5]2[S:10][C:9]([CH:11]=[C:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:41]=[CH:40][CH:39]=[C:38]3[C:34]=2[CH:35]=[N:36][NH:37]3)O1>>[NH:37]1[C:38]2[C:34](=[C:33]([C:2]3[N:3]=[C:4]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[C:5]4[S:10][C:9]([CH:11]=[C:12]5[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]5)=[CH:8][C:6]=4[N:7]=3)[CH:41]=[CH:40][CH:39]=2)[CH:35]=[N:36]1

Participants

3

Reactant 2

HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 866183992-Chloro-6-(1-methyl-piperidin-4-ylidenemethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Product 1

HCID 595929482-(1H-indazol-4-yl)-6-((1-methylpiperidin-4-ylidene)methyl)-4-morpholinothieno[3,2-d]pyrimidine

Procedure

2-Chloro-6-(1-methyl-piperidin-4-ylidenemethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine was reacted with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole in general procedure A. Purification on silica yielded 181. NMR: (CDCl3) 2.37 (3H, s); 2.55 (6H, m); 2.82 (2H, t, J=5.5 Hz); 3.93 (4H, t, J=4.8 Hz); 4.10 (4H, t, J=4.8 Hz); 6.44 (1H, s); 7.33 (1H, s); 7.51 (1H, s); 7.60 (1H, d, J=8.2 Hz); 8.28 (1H, d, J=7.1 Hz); 9.03 (1H, s); 10.25 (br s). M+H (447)

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-ef9e20565e814d3cb2d1f846282eea90
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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