Hydrochloric Acid → (3,4-Diethoxy-phenyl)-[7-(4-methanesulfonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl]-amine

HRID 1966394Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[CH:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH3:33])[NH2:27])[CH3:22].Cl>C(O)CCC>[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([NH:27][C:2]2[N:3]=[CH:4][C:5]3[CH:10]=[CH:9][N:8]([C:11]4[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=4)[C:6]=3[N:7]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH3:33])[CH3:22]

Participants

Conditions

Temperature: 140 °C

Procedure

To a suspension of 2-chloro-7-(4-methanesulfonyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidine (30.0 mg, 0.093 mmol) in BuOH (1.5 mL) is added 3,4-diethoxyaniline (41.0 mg, 0.220 mmol) and concentrated aqueous HCl (37%, 23.0 μL, 0.232 mmol). The reaction mixture is heated to 140° C. for 24 h, cooled to rt, and concentrated under reduce pressure. The residue is purified by reverse phase prep-HPLC (Waters) to afford the title compound (1) as a yellow solid. HPLC: tR=1.61 min (Method A); MS-ES: (M+H)+=453.

Workup

temperaturecooled to rt
concentrationconcentrated
customThe residue is purified by reverse phase prep-HPLC (Waters)

Sources & evidence

ORD record: ord-478a095e8da44969a08f4598f81eb10a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420657B2

Reaction notes

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