Potassium Carbonate → N1-(2-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-N2-(2,4-difluorophenyl)-N1,N2-dimethylethane-1,2-diamine

HRID 639485Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[C:8]2[N:9]=[C:10]([NH2:14])[N:11]=[C:12]([Cl:13])[C:7]=2[CH:6]=[CH:5]1.[CH3:15][NH:16][CH2:17][CH2:18][N:19]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=1[F:28])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:14][C:10]1[N:11]=[C:12]([Cl:13])[C:7]2[CH:6]=[CH:5][N:4]([CH2:3][CH2:2][N:16]([CH3:15])[CH2:17][CH2:18][N:19]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[F:28])[CH3:20])[C:8]=2[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the title A compound, 7-(2-bromoethyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (206.4 mg, 0.75 mmol) and N-(2,4-difluorophenyl)-N,N′-dimethylethylene-1,2-diamine (150 mg, 0.75 mmol) in 5.0 mL of anhydrous acetone is added potassium carbonate (311 mg, 2.25 mmol) at RT under positive N2 pressure. The mixture is stirred at 50° C. for 24 h. The solvent is removed in vacuo after the reaction mixture is cooled down to RT. The residue is absorbed directly onto silica gel and chromatographed to yield N1-(2-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)ethyl)-N2-(2,4-difluorophenyl)-N1,N2-dimethylethane-1,2-diamine as a brown gummy solid.

Workup

customThe solvent is removed in vacuo after the reaction mixture
temperatureis cooled down to RT
customThe residue is absorbed directly onto silica gel
customchromatographed

Sources & evidence

ORD record: ord-a49b5e3d791c485cadf6b07785072045
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691869B2

Reaction notes

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