2,4-Dichloro-1,3,5-triazine → HCID 22496132, compound

HRID 1815900Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH3:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH2:24][CH2:23][CH2:22]2>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:25]2[C:26]3[C:21](=[CH:20][C:19]([CH3:18])=[CH:28][CH:27]=3)[CH2:22][CH2:23][CH2:24]2)[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (1.95 g, 13 mmol) was dissolved in DMF (50 mL) under N2 and cooled to 0° C. DIEA (1.68 g, 13 mmol) was added, followed by the addition of 6-methyl-1,2,3,4-tetrahydroquinoline (1.91 g, 13 mmol). The reaction was stirred with gradual warming to RT. The reaction was quenched after 3 h with water, which causes a sticky precipitate to form. The mixture was extracted 3× with EtOAc. The EtOAc extracts were washed brine, combined, dried over Na2SO4, filtered, and concentrated, then dried under high vacuum to remove residual traces of DMF. The recovered material was purified by elution through a 17×2.5 cm column of silica gel (5%, 10%, 20% and 40% EtOAc/Hexane step gradient) giving 1-(4-chloro-[1,3,5]triazin-2-yl)-6-methyl-1,2,3,4-tetrahydro-quinoline as a white solid.

Workup

temperaturewith gradual warming to RT
customThe reaction was quenched after 3 h with water, which
customto form
extractionThe mixture was extracted 3× with EtOAc
washThe EtOAc extracts were washed brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customdried under high vacuum
customto remove residual traces of DMF
customThe recovered material was purified by elution through a 17×2.5 cm column of silica gel (5%, 10%, 20% and 40% EtOAc/Hexane step gradient)

Sources & evidence

ORD record: ord-758b8fdd45644b3fa236090fa76fcfee
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881737B2

Reaction notes

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