4-Chloro-6-(ethylamino)pyrimidine → N-Ethyl-N'-[4-(4-methyl-piperazin-1-yl)-phenyl]-pyrimidine-4,6-diamine

HRID 1038710Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH3:10])[CH:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1>O.C(O)(=O)C>[CH2:9]([NH:8][C:4]1[CH:3]=[C:2]([NH:22][C:21]2[CH:20]=[CH:19][C:18]([N:15]3[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH2:16]3)=[CH:24][CH:23]=2)[N:7]=[CH:6][N:5]=1)[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (6-chloro-pyrimidin-4-yl)-ethyl-amine (363 mg, 2.30 mmol, 1.1 eq.) and 4-(4-methylpiperazin-1-yl)-aniline (400 mg, 2.09 mmol) in water (0.8 ml) and glacial acetic acid (3.2 ml) is heated to 100° C. 3 h. After solvent evaporation, the residue is taken up in methanol, made alkaline by addition of 25% NH3 in water and concentrated. The residue is purified by MPLC (silica gel) (DCM/MeOH) to afford 395 mg of the title compound as a white solid: ESI-MS: 313.2 [MH]+; tR=1.25 min (purity: ˜90%, gradient J); TLC: Rf=0.12 (DCM/MeOH, 9:1).

Workup

custom3 h
customAfter solvent evaporation
additionby addition of 25% NH3 in water
concentrationconcentrated
customThe residue is purified by MPLC (silica gel) (DCM/MeOH)

Sources & evidence

ORD record: ord-9f9bd54f83fa4b75bdd4cc84f9a431a6
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552002B2

Reaction notes

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