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

HRID 1038746Notes

Reaction equation

HRID 1038746 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:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)[CH2:13]C.[CH2:28](N(C(C)C)C(C)C)C>CCO>[CH3:9][NH:8][C:4]1[N:3]=[C:2]([NH:25][C:24]2[CH:23]=[CH:22][C:21]([N:18]3[CH2:17][CH2:16][N:15]([CH:12]([CH3:13])[CH3:28])[CH2:20][CH2:19]3)=[CH:27][CH:26]=2)[N:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 91615414-(4-Propylpiperazin-1-yl)anilineHCID 179596504-Chloro-N-methyl-1,3,5-triazin-2-amine

Product 1

HCID 66669997N-Methyl-N'-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-[1,3,5]triazine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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-propylpiperazin-1-yl)-aniline (500 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. Workup as described in Example 228A gives the title compound: ESI-MS: 328 [MH]+; TLC: Rf=0.14 (DCM/MeOH, 9:1).

Sources & evidence

ORD record
ord-b40ddb22a71f452eb41fceaa2a45c0c0
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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