Potassium Carbonate → HCID 59645279, compound

HRID 2252795Notes

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.[C:27]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:30]([O:29][C:27]([N:34]1[CH2:39][CH2:38][N:37]([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)[CH2:36][CH2:35]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1.6 g (4 mmol) [6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine (for the preparation see Example 9, Step 9.3 of WO 03/013541 A1) in 50 ml DMF is treated with 1.56 g (8.4 mmol) N—BOC-piperazine and 2.76 g (20 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 95:5 and then dichloromethane/ethanol 9:1. The title compound is obtained as a solid; m.p. 244-246° C.; MS-ES+: (M+H)+=513; TLC Rf(dichloromethane/ethanol 9:1) 0.46.

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

Sources & evidence

ORD record: ord-e71f314ab44b4139ae93591b9524df4d
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07323469B2

Reaction notes

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