Aluminum(III) Chloride → HCID 57693558, compound

HRID 1516847Notes

Reaction equation

C([N:8]1[C:16]2[C:15]([S: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[S: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-(mesitylthio)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (9.2 mg, 0.03 mmol) in 1,2-dichlorobenzene (1 mL) was added AlCl3 (26 mg, 0.3 mmol). The reaction mixture was heated at 160° C. for 1.5 h, 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 preparative TLC, eluting with Hexanes:Ethyl acetate (2.5:1) produced the product as a pink solid (7.7 mg, 20%).

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 preparative TLC
washeluting with Hexanes:Ethyl acetate (2.5:1)

Sources & evidence

ORD record: ord-be9b6329e39c4e5eb00a41f71bbafe63
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227601B2

Reaction notes

Loading…