Ammonium Hydroxide → 6-(3-(6-Methoxypyridin-3-ylamino)pyrazin-2-yl)-2-methylpyrimidin-4-amine

HRID 1811924Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[CH:21]=[C:20](S(C)=O)[N:19]=[C:18]([CH3:25])[N:17]=3)=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[OH-].[NH4+:27]>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([C:16]3[N:17]=[C:18]([CH3:25])[N:19]=[C:20]([NH2:27])[CH:21]=3)=[N:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A glass microwave reaction vessel was charged with N-(6-methoxypyridin-3-yl)-3-(2-methyl-6-(methylsulfinyl)pyrimidin-4-yl)pyrazin-2-amine (11.40 mg, 0.032 mmol) (crude product from the last step) and ammonium hydroxide, 28.0-30.0% (0.5 mL, 12.84 mmol) in dioxane (1 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 2 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 80% EtOAc/hexanes to give 6-(3-(6-methoxypyridin-3-ylamino)pyrazin-2-yl)-2-methylpyrimidin-4-amine (8.2 mg, 0.027 mmol, 83% yield). 1H NMR (300 MHz, CDCl3) δ 12.46 (s, 1H); 8.42 (s, 1H); 8.15 (s, 1H); 8.10 (dd, J=8.77, 2.48 Hz, 1H); 7.98 (d, J=1.32 Hz, 1H); 7.47 (s, 1H); 6.78 (d, J=8.62 Hz, 1H); 4.95 (s, 2H); 3.95 (s, 3H); 2.64 (s, 3H). m/z (ESI, +ve ion) 310.1 (M+H)+.

Workup

customA glass microwave reaction vessel
customThe solvent was removed in vacuo
customthe residue was purified by silica gel chromatography
washeluting with 80% EtOAc/hexanes

Sources & evidence

ORD record: ord-fb418a6e01b0460298f1b0032f96d587
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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