Ammonia → 3-(6-amino-2-methylpyrimidin-4-yl)-N-(1H-indazol-4-yl)quinoxalin-2-amine

HRID 1621654Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[C:5]([NH:10][C:11]3[C:20]([C:21]4[CH:26]=[C:25](S(C)=O)[N:24]=[C:23]([CH3:30])[N:22]=4)=[N:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[NH3:31]>O1CCOCC1>[NH2:31][C:25]1[N:24]=[C:23]([CH3:30])[N:22]=[C:21]([C:20]2[C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[CH:3]=[N:2][NH:1]4)=[N:12][C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with N-(1H-indazol-4-yl)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-yl)quinoxalin-2-amine (36 mg, 0.087 mmol) in dioxane (2 mL), ammonia was bubbled in for 5 minutes. The reaction mixture was stirred and heated at 100° C. for 4 h. More NH3 was bubbled in and the mixture was heated for an additional 2 h. The mixture was cooled to room temperature and concentrated in vacuo. Prep TLC purification (5% MeOH in DCM as developed reagent) gave 3-(6-amino-2-methylpyrimidin-4-yl)-N-(1H-indazol-4-yl)quinoxalin-2-amine (10 mg, 0.027 mmol, 31.3% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 13.22 (s, 2H); 8.52 (d, J=7.07 Hz, 1H); 8.31 (s, 1H); 7.95 (d, J=8.09 Hz, 1H); 7.82 (d, J=9.10 Hz, 1H); 7.72-7.80 (m, 1H); 7.64 (s, 1H); 7.55-7.62 (m, 1H); 7.34-7.46 (m, 2H); 7.26 (d, J=9.10 Hz, 1H); 2.70 (s, 3H). m/z (ESI, +ve ion) 369 (M+H)+.

Workup

customA glass microwave reaction vessel
customwas bubbled in for 5 minutes
customMore NH3 was bubbled in and the mixture
temperaturewas heated for an additional 2 h
temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo
customPrep TLC purification (5% MeOH in DCM as developed reagent)

Sources & evidence

ORD record: ord-e72034c15ce64f4d8ce0681bd77fad2c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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