Aluminum(III) Chloride → HCID 11962295, compound

HRID 1516841Notes

Reaction equation

C([N:8]1[C:16]2[C:15]([O:17][C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])=[N:14][C:13]([NH:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=3)=[N:12][C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[C:19]1([CH3:26])[CH:20]=[C:21]([CH3:25])[CH:22]=[C:23]([CH3:24])[C:18]=1[O:17][C:15]1[C:16]2[NH:8][CH:9]=[CH:10][C:11]=2[N:12]=[C:13]([NH:27][C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[N:14]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a suspension of 4-(5-benzyl-4-(mesityloxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (150 mg, 0.33 mmol) in 1,2-dichlorobenzene (13 mL) was added AlCl3 (436 mg, 3.27 mmol). The reaction mixture was heated at 160° C. for 1.5 h during which the reaction mixture became dark and homogeneous. Upon completion of the reaction, the reaction mixture was cooled and washed with NH4Cl. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with Hexanes:Ethyl acetate (5:1-1:1) provided the product as a tan solid (27.8 mg, 23%).

Workup

customUpon completion of the reaction
temperaturethe reaction mixture was cooled
washwashed with NH4Cl
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified by column chromatography
washeluting with Hexanes:Ethyl acetate (5:1-1:1)

Sources & evidence

ORD record: ord-08ffa2f551854d738f886f0b42acd00e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227601B2

Reaction notes

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