Potassium Carbonate → HCID 10137305, compound

HRID 1295638Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 10.8 g (30 mmol) [6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine in 450 ml DMF is treated with 6.8 ml (63 mmol) N-methylpiperazine and 20.7 g (150 mmol) anhydrous potassium carbonate and the mixture heated to 65° C. for 1 hour. The reaction mixture is cooled and the inorganic salts removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland). The DMF is evaporated under reduced pressure and the residue purified through flash chromatography using first dichloromethane/ethanol 9:1 and then dichloromethane/ethanol 9:1 plus 1% conc. ammonia. Crystallization of the pure fractions from THF (20 ml) and hexanes (80 ml) gives the title compound; m.p. 248-250° C.; MS-ES+: (M+H)+=427.

Workup

temperatureThe reaction mixture is cooled
customthe inorganic salts removed by filtration (Hyflo Super Cel®; Fluka, Buchs, Switzerland)
customThe DMF is evaporated under reduced pressure
customthe residue purified through flash chromatography
customCrystallization of the pure fractions from THF (20 ml) and hexanes (80 ml)

Sources & evidence

ORD record: ord-cbefe679ab6b44f1ac9137f693506d10
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244729B2

Reaction notes

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