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

HRID 1931194Notes

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-bc118acfc5744e4aaab155a36e5f7536
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188273B2

Reaction notes

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