Ethanol → HCID 59548455, compound

HRID 1621485Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH2:15])[CH:9]=1.[NH:16]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([NH2:25])[C:19]=2[CH:18]=[N:17]1.CCO>C([O-])(O)=O.[Na+]>[NH2:15][C:10]1[N:11]=[C:12]([CH3:14])[N:13]=[C:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[NH:25][C:20]2[C:19]3[CH:18]=[N:17][NH:16][C:24]=3[CH:23]=[CH:22][CH:21]=2)[CH:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A glass microwave reaction vessel was charged with 6-(4-chloropyridin-3-yl)-2-methylpyrimidin-4-amine (22 mg, 100 μmol), 1H-indazol-4-amine (27 mg, 199 μmol, Bionet) and EtOH (1 mL). The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 160° C. for 30 min. The reaction mixture was diluted with saturated NaHCO3 (2 mL) and extracted with EtOAc (3×20 mL). The organic extract was washed with saturated NaCl (2 mL), dried over Na2SO4, filtered, concentrated and the residue was purified by silica gel chromatography, eluting with 10% MeOH/CH2Cl2/1% NH4OH to give N-(3-(6-amino-2-methylpyrimidin-4-yl)pyridin-4-yl)-1H-indazol-4-amine (14 mg, 44% yield). 1H NMR (300 MHz, CD3OD) δ 8.71 (s, 1H); 8.19 (d, J=6.14 Hz, 1H); 7.34-7.53 (m, 2H); 7.29 (d, J=7.02 Hz, 1H); 7.18 (d, J=6.28 Hz, 1H); 6.90 (s, 1H); 2.59 (s, 3H). m/z (ESI, +ve ion) 318 (M+H)+.

Workup

customA glass microwave reaction vessel
extractionextracted with EtOAc (3×20 mL)
extractionThe organic extract
washwas washed with saturated NaCl (2 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customthe residue was purified by silica gel chromatography
washeluting with 10% MeOH/CH2Cl2/1% NH4OH

Sources & evidence

ORD record: ord-bf44e39d44634ee2920ad910997097ee
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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