Water → HCID 44194119, compound

HRID 876913Notes

Reaction equation

HRID 876913 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.[NH:21]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[N:22]1.O>C(Cl)Cl>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([NH:12][C:4]2[N:3]=[C:2]([C:24]3[CH:25]=[N:21][NH:22][CH:23]=3)[N:7]=[C:6]3[N:8]([CH3:11])[N:9]=[CH:10][C:5]=23)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 462617946-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 44194119HCID 44194119, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-N-(3-methoxyphenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 6 was reacted with pyrazole-4-boronic acid pinacol ester using General Procedure A. Addition of water and CH2Cl2 to the reaction, followed by sonication and filtration yielded 101. NMR: (CDCl3): 3.87 (s, 3H, CH3), 4.07 (s, 3H, CH3), 6.87 (dd, H, ArH, J=2.4, 8.37), 7.13 (d, H, ArH, J=7.85), 7.29 (m, H, ArH), 7.37 (t, H, ArH, J=8.13), 7.43 (s, H, ArH), 8.37 (s, 2H, 2×ArH). MS: (ESI+) MH+==322.23

Workup

  1. customto the reaction
  2. customfollowed by sonication and filtration

Sources & evidence

ORD record
ord-f86fe505296246688c43928f80512c26
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

Loading…