5-(Aminomethyl)-2-chloropyridine → 6-Chloro-N-(6-chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethylphenyl)-1,3,5-triazine-2,4-diamine

HRID 563848Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)[N:3]=1.[Cl:21][C:22]1[N:27]=[CH:26][C:25]([CH2:28][NH2:29])=[CH:24][CH:23]=1>O1CCOCC1.O.C(OCC)(=O)C>[Cl:8][C:6]1[N:7]=[C:2]([NH:29][CH2:28][C:25]2[CH:26]=[N:27][C:22]([Cl:21])=[CH:23][CH:24]=2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)[N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of (4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)amine (XVII) (2.0 g, 6.11 mmol) in dioxane (5 mL) was added i-Pr2(Et)N (0.832 g, 6.44 mmol) and (6-chloropyridin-3-yl)methylamine (0.912 g, 6.44 mmol), and the mixture heated at 50° C. for 12 h. The mixture was cooled to ambient temperature and diluted with water and ethyl acetate. The organic phase was separated, washed with brine and concentrated under vacuum to give 1 6-chloro-N-(6-chloropyridin-3-ylmethyl)-N′-(4-fluoro-3-trifluoromethylphenyl)-1,3,5-triazine-2,4-diamine (XVIII) (1.60 g (60% yield): 1H NMR (DMSO) δ 8.32 (bs, 1H), 7.98 (bs, 1H), 7.58 (bd, 1H), 7.28 (m, 3H), 7.16 (t, J=9.0 Hz, 1H), 6.60 (bs, 1H), 4.64 (m, 2H); ESI/MS 433 (M+H), 431 (M−H).

Workup

temperatureThe mixture was cooled to ambient temperature
customThe organic phase was separated
washwashed with brine
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-087bfaee4b1c4138aa85237d61b9775c
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067588B2

Reaction notes

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