3-amino-N,N-dimethylbenzylamine → N-(3-Dimethylaminomethyl-phenyl)-N'-ethyl-pyrimidine-4,6-diamine

HRID 1038722Notes

Reaction equation

HRID 1038722 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[CH:9][CH:10]=1)[CH3:3].Cl[C:13]1[N:18]=[CH:17][N:16]=[C:15]([NH:19][CH2:20][CH3:21])[CH:14]=1>>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([NH:11][C:13]2[CH:14]=[C:15]([NH:19][CH2:20][CH3:21])[N:16]=[CH:17][N:18]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:1]

Participants

3

Reactant 2

HCID 992943-amino-N,N-dimethylbenzylamineHCID 5884524-Chloro-6-(ethylamino)pyrimidine

Product 1

HCID 66669989N-(3-Dimethylaminomethyl-phenyl)-N'-ethyl-pyrimidine-4,6-diamine

Conditions

Temperature
160 °C

Procedure

The title compound is prepared as described in Example 143A but using 3-dimethylaminomethyl-phenylamine (334 mg, 2.20 mmol, 1 eq.), (6-chloro-pyrimidin-4-yl)-ethyl-amine (Example 143B) and stirring the reaction mixture for 3 h at 160° C. Purification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) followed by trituration of the resulting solid in diethyl ether, affords 335 mg of the title compound as a beige solid: ESI-MS: 272.1 [MH]+; tR=1.18 min (purity: 100%, gradient J); TLC: Rf=0.16 (DCM/MeOH+1% NH3aq, 9:1).

Workup

  1. customThe title compound is prepared
  2. customPurification of the crude product by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Sources & evidence

ORD record
ord-a1312b76d9c44b0e8e26450960dfd7bb
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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