1-Ethylpiperazine → (3-Chloro-benzyl)-{6-[4-(4-ethyl-piperazin-1-ylmethyl)-phenyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-amine

HRID 2252775Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][CH:17]=3)[NH:13][C:9]=2[N:10]=[CH:11][N:12]=1.[CH2:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[CH3:28]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:32]4[CH2:33][CH2:34][N:29]([CH2:27][CH3:28])[CH2:30][CH2:31]4)=[CH:18][CH:17]=3)[NH:13][C:9]=2[N:10]=[CH:11][N:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

(3-Chloro-benzyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine (150 mg, 0.35 mmol) is suspended in 5 ml dioxane and treated with N-ethyl-piperazine. The mixture is heated to 90° C. for 7 h. The solvent is evaporated and the residue is purified by flash chromatography on 34 g of silica gel. The column is eluted using a mixture of dichloromethane/methanol with gradually increasing concentrations of methanol starting with 100:1.25 and ending with 100:5 and then switching to dichloromethane/methanol/conc. ammonia starting with 100:5:0.25 and ending with 100:10:0.5. Fractions containing the title compound were pooled and concentrated on a rotary evaporator to give the title compound; m.p. 241-243° C.; MS-ES+: (M+H)+=461.

Workup

customThe solvent is evaporated
customthe residue is purified by flash chromatography on 34 g of silica gel
washThe column is eluted
additiona mixture of dichloromethane/methanol
temperaturewith gradually increasing concentrations of methanol starting with 100:1.25
additionFractions containing the title compound
concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record: ord-fc1bd50fe85e4ea7886d7cb4edc07458
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323469B2

Reaction notes

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