4-(4-Ethylpiperazin-1-yl)aniline → N4-(4-(4-Ethyl-1-piperazinyl)phenyl)-N6-methyl-4,6-pyrimidinediamine

HRID 1038714Notes

Reaction equation

HRID 1038714 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].ClC1C(OC)=CC=C(Cl)C=1N[C:27](=O)[N:28](C)[C:29]1[CH:34]=[C:33](NC2C=CC(N3CCN(C)CC3)=CC=2)[N:32]=[CH:31][N:30]=1>>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:33]3[CH:34]=[C:29]([NH:28][CH3:27])[N:30]=[CH:31][N:32]=3)=[CH:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

3

Reactant 2

HCID 9367384-(4-Ethylpiperazin-1-yl)anilineHCID 565947453-(2,6-Dichloro-3-methoxy-phenyl)-1-methyl-1-(6-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl)-urea

Product 1

HCID 56594616N4-(4-(4-Ethyl-1-piperazinyl)phenyl)-N6-methyl-4,6-pyrimidinediamine

Procedure

The title compound is prepared as described in Example 144A but using 4-(4-ethylpiperazin-1-yl)-aniline (1 g, 4.88 mmol) and (6-chloro-pyrimidin-4-yl)-methyl-amine (Example 1) (771 1.81 g, 12.68 mmol, 1.3 eq.). Purification of the residue by silica gel column chromatography (DCM/MeOH, 93:7) followed by trituration in diethyl ether affords the title compound as a white solid: ESI-MS: 313.2 [MH]+; tR=1.10 min (gradient J); TLC: Rf=0.21 (DCM/MeOH, 93:7).

Workup

  1. customThe title compound is prepared
  2. customPurification of the residue by silica gel column chromatography (DCM/MeOH, 93:7)

Sources & evidence

ORD record
ord-1edcfa01f07349a1b64b2e634d161e6a
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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