Chloroform → 4-(4-(4-Acetyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

HRID 1805878Notes

Reaction equation

[C:1]([C:4]1[CH:35]=[C:34]([CH3:36])[C:7]([O:8][C:9]2[C:10]3[N:26](CC4C=CC=CC=4)[CH:25]=[CH:24][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[N:14]=2)=[C:6]([CH3:37])[CH:5]=1)(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)(Cl)Cl>ClC1C=CC=CC=1Cl>[C:1]([C:4]1[CH:5]=[C:6]([CH3:37])[C:7]([O:8][C:9]2[C:10]3[NH:26][CH:25]=[CH:24][C:11]=3[N:12]=[C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=3)[N:14]=2)=[C:34]([CH3:36])[CH:35]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

To a suspension of 4-(4-(4-acetyl-2,6-dimethylphenoxy)-5-benzyl-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile (65 mg, 0.13 mmol) in 1,2-dichlorobenzene (5.3 mL) was added AlCl3 (178 mg, 1.3 mmol). The reaction mixture was heated at 160° C. for 1.5 h, after which time the reaction mixture became dark and homogeneous. Upon completion of the reaction, the reaction mixture was cooled, CHCl3 was added, and the mixture was 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 silica gel column chromatography, eluting with hexanes:ethyl acetate (3:1), to give the product as a brown solid (41 mg, 77%).

Workup

customUpon completion of the reaction
temperaturethe reaction mixture was cooled
washthe mixture was washed 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 silica gel column chromatography
washeluting with hexanes:ethyl acetate (3:1)

Sources & evidence

ORD record: ord-e14db315f8bf4100b31ebd6c36042a65
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354532B2

Reaction notes

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