N4-(4-(4-Ethyl-1-piperazinyl)phenyl)-N6-methyl-4,6-pyrimidinediamine → BGJ-398

HRID 2176868Notes

Reaction equation

HRID 2176868 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[N:13]=[C:14]=[O:15].[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([NH:30][C:31]3[CH:36]=[C:35]([NH:37][CH3:38])[N:34]=[CH:33][N:32]=3)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH3:17]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[NH:13][C:14](=[O:15])[N:37]([C:35]1[CH:36]=[C:31]([NH:30][C:27]2[CH:26]=[CH:25][C:24]([N:21]3[CH2:20][CH2:19][N:18]([CH2:16][CH3:17])[CH2:23][CH2:22]3)=[CH:29][CH:28]=2)[N:32]=[CH:33][N:34]=1)[CH3:38]

Participants

4

Reactant 2

HCID 56594616N4-(4-(4-Ethyl-1-piperazinyl)phenyl)-N6-methyl-4,6-pyrimidinediamineHCID 860869932,6-Dichloro-3,5-dimethoxyphenyl isocyanate

Product 1

HCID 53235510BGJ-398

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The title compound was prepared by adding 2,6-dichloro-3,5-dimethoxyphenyl-isocyanate (1.25 eq.) to a solution of N-[4-(4-ethyl-piperazin-1-yl)-phenyl]-N′-methyl-pyrimidine-4,6-diamine (2.39 g, 7.7 mmol, 1 eq.) in toluene and stirring the reaction mixture for 1.5 h at reflux. Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5) affords the title compound as a white solid: ESI-MS: 560.0/561.9 [MH]+; tR=3.54 min (purity: 100%, gradient J); TLC: Rf=0.28 (DCM/MeOH+1% NH3aq, 95:5). Analysis: C26H31N7O3Cl2, calc. C, 55.72%; H, 5.57%; N, 17.49%; O, 8.56%; Cl, 12.65%. Found C, 55.96%; H, 5.84%; N, 17.17%; O, 8.46%; Cl, 12.57%. The title compound was characterized by XRPD, thermal and other methods as described below.

Workup

  1. customThe title compound was prepared
  2. temperatureat reflux
  3. customPurification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 95:5)

Sources & evidence

ORD record
ord-35e3f060db1b4e85bef87a33ad141e40
Source dataset
uspto-grants-2015_06
Patent number
US09067896B2

Reaction notes

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