Hydrochloric Acid → N4-(4-(4-Ethyl-1-piperazinyl)phenyl)-N6-methyl-4,6-pyrimidinediamine

HRID 2066718Notes

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].Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]([NH:23][CH3:24])[CH:18]=1.Cl>O1CCOCC1>[CH2:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:17]3[CH:18]=[C:19]([NH:23][CH3:24])[N:20]=[CH:21][N:22]=3)=[CH:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-(4-ethylpiperazin-1-yl)-aniline (1 g, 4.88 mmol) (prepared in analogy to Example 238, Step 238.1), (6-chloro-pyrimidin-4-yl)-methyl-amine (1.81 g, 12.68 mmol, 1.3 eq.) and 4N HCl in dioxane (15 ml) is heated in a sealed tube to 150° C. for 5 h. The reaction mixture is concentrated, diluted with DCM and a saturated aqueous solution of sodium bicarbonate. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. 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 (system 1); TLC: Rf=0.21 (DCM/MeOH, 93:7).

Workup

concentrationThe reaction mixture is concentrated
additiondiluted with DCM
customThe aqueous layer is separated
extractionextracted with DCM
washThe organic phase is washed with brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated
customPurification of the residue by silica gel column chromatography (DCM/MeOH, 93:7)

Sources & evidence

ORD record: ord-d2ced6111e7b4092b9f5ac102f877b5c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293746B2

Reaction notes

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