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

HRID 1621522Notes

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][O: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][O: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-morpholinopyrimidin-4-amine (34 mg, 0.080 mmol), ammonia (0.5 mL, 23.11 mmol) (30% in water) and dioxane (1 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 16 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-morpholinopyrimidin-5-yl)-6-methyl-1,3,5-triazin-2-amine (22 mg, 0.056 mmol, 69.8% yield). 1H NMR (300 MHz, d6-DMSO) δ 11.91 (s, 1H); 9.16 (s, 1H); 8.50 (s, 1H); 8.08 (d, J=4.97 Hz, 1H); 7.67 (s, 1H); 7.51 (s, 1H); 6.85 (d, J=8.77 Hz, 1H); 3.85 (s, 3H); 3.74 (s, 4H); 3.66 (s, 4H); 2.36 (s, 3H). m/z (ESI, +ve ion) 396.0 (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-3422a3e58c7e44579d63d12eba90edaa
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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