(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-methoxy-ethyl)-amine → 6-(1H-indazol-4-yl)-N-(2-methoxyethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 876930Notes

Reaction equation

HRID 876930 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][CH2:13][CH2:14][O:15][CH3:16])[N:3]=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](B2OC(C)(C)C(C)(C)O2)=[N:18]1>>[NH:17]1[C:25]2[C:20](=[C:21]([C:2]3[N:7]=[C:6]4[N:8]([CH3:11])[N:9]=[CH:10][C:5]4=[C:4]([NH:12][CH2:13][CH2:14][O:15][CH3:16])[N:3]=3)[CH:22]=[CH:23][CH:24]=2)[CH:19]=[N:18]1

Participants

3

Reactant 2

HCID 58345940(6-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-methoxy-ethyl)-amineHCID 178431105HCID 178431105, compound

Product 1

HCID 441800206-(1H-indazol-4-yl)-N-(2-methoxyethyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Procedure

(6-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-(2-methoxy-ethyl)-amine was reacted with indazole boronic acid pinacol ester in General Procedure A. Purification on silica yielded 130. NMR: (CDCl3): 3.48 (s, 3H, CH3), 3.77 (t, H, ArH, J=5.13 Hz), 4.04 (m, 2H, CH2), 4.18 (s, 3H, CH3), 5.80 (sbr, H, NH), 7.53 (t, H, ArH, J=7.29 Hz), 7.63 (d, H, ArH, J=8.29 HZ), 7.95 (s, H, ArH), 8.43 (d, H, ArH, J=7.24 Hz), 9.17 (s, H, ArH), 10.2 (sbr, H, NH). MS: (ESI+) MH+=324.14

Workup

  1. customPurification on silica

Sources & evidence

ORD record
ord-5148d8e0e5d7409989d744924c0b6466
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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