Methanol → 4-(2-(6-Methoxypyridin-3-ylamino)-5-(morpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

HRID 1811826Notes

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][C:13]([CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:12][N:11]=2)=[CH:5][CH:4]=1.CO.[NH3:34].CC(O)C>C(Cl)Cl>[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]([NH2:34])[N:17]=3)=[CH:14][C:13]([CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:12][N:11]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A stirred mixture of N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine (19 mg, 0.043 mmol) in 2.0 M NH3/iPrOH (3.0 mL) was sealed and heated at 90° C. for 24 h. The reaction mixture was concentrated and the crude product was adsorbed onto a plug of silica gel and chromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr., pre-packed silica gel column (DCM to 5% MeOH in DCM) to give 4-(2-(6-methoxypyridin-3-ylamino)-5-(morpholinomethyl)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (6.00 mg, 0.015 mmol, 34.0% yield) as a yellow solid. LCMS (API-ES) m/z 409 (M+H)+; 1H NMR (400 MHz, CDCl3, with one drop of d6-DMSO) δ 11.69 (br. s., 1H) 8.76 (br. s., 1H) 8.39 (br. s., 1H) 8.23 (br. s., 1H) 8.12 (br. s., 1H) 6.77 (d, J=9.00 Hz, 1H) 5.92 (br. s., 2H) 3.93 (br. s., 3H) 3.49 (br. s., 2H) 2.55 (br. s., 3H) 2.50 (br. s., 4H) 2.23 (br. s., 4H).

Workup

customwas sealed
concentrationThe reaction mixture was concentrated
customchromatographed through a RediSep®, Teledyne ISCO, Lincoln, Nebr

Sources & evidence

ORD record: ord-a4e8c98d5bbe4468864aa1d0075f4284
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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