Sodium Iodide → N-Methyl-N'-[4-(4-ethyl-piperazin-1-yl)-phenyl]-[1,3,5]triazine-2,4-diamine

HRID 1038744Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH3:9])[N:3]=1.[Na+].[I-].[CH2:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[CH3:13].C(N(C(C)C)C(C)C)C>CCO>[CH3:9][NH:8][C:4]1[N:3]=[C:2]([NH:24][C:23]2[CH:22]=[CH:21][C:20]([N:17]3[CH2:16][CH2:15][N:14]([CH2:12][CH3:13])[CH2:19][CH2:18]3)=[CH:26][CH:25]=2)[N:7]=[CH:6][N:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (4-chloro-[1,3,5]triazin-2-yl)-methyl-amine (290 mg, 2.00 mmol), NaI (28 mg) and 4-(4-ethylpiperazin-1-yl)-aniline (410 mg, 2.0 mmol) in EtOH (20 ml) and N-ethyl-diisopropyl amine (350 μl, 2.0 mmol) is heated to 80° C. for 3 h under a nitrogen atmosphere. The reaction mixture is cooled to RT, concentrated partially in vacuo and diluted with hexane at 0° C. The precipitate is filtered off, washed with Et2O and re-dissolved in EE and water. The separated off aqueous phase is extracted twice with EE, the organic layer washed with water and brine, dried (Na2SO4) and concentrated, yielding the title compound: ESI-MS: 314 [MH]+; TLC: Rf=0.10 (DCM/MeOH 9:1).

Workup

temperatureThe reaction mixture is cooled to RT
concentrationconcentrated partially in vacuo
additiondiluted with hexane at 0° C
filtrationThe precipitate is filtered off
washwashed with Et2O
dissolutionre-dissolved in EE and water
customThe separated off aqueous phase
extractionis extracted twice with EE
washthe organic layer washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-fbf41a1738384083a8516324d2d34722
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552002B2

Reaction notes

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