Ammonia → 4-(4-(6-Methoxypyridin-3-ylamino)-2-(piperidin-1-yl)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811944Notes

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[N:21]=[C:20]([CH3:22])[N:19]=[C:18](SC)[N:17]=3)=[CH:14][N:13]=[C:12]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:11]=2)=[CH:5][CH:4]=1.[NH3:31]>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:21]=[C:20]([CH3:22])[N:19]=[C:18]([NH2:31])[N:17]=3)=[CH:14][N:13]=[C:12]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[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)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-2-(piperidin-1-yl)pyrimidin-4-amine (22 mg, 0.052 mmol), ammonia (0.5 mL, 30% in water) and dioxane (2 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 23 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with EtOAc to give 4-(4-(6-methoxypyridin-3-ylamino)-2-(piperidin-1-yl)pyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine (18 mg, 0.046 mmol, 88% yield). 1H NMR (300 MHz, CDCl3) δ 11.88 (s, 1H); 9.27 (s, 1H); 8.35 (s, 1H); 7.97-8.06 (m, J=8.18, 1.46 Hz, 1H); 6.76 (d, J=8.92 Hz, 1H); 5.21 (s, 2H); 3.95 (s, 3H); 3.83 (s, 4H); 2.48 (s, 3H); 1.57-1.76 (m, 6H). m/z (ESI, +ve ion) 394.1 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-77be24b4478740649d1979e31f84a6d9
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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