Potassium Carbonate → HCID 66998732, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][C@H:20]2[C@H:18]([CH2:19]2)[C@H:17]1[CH2:22][NH2:23])=[O:15])([CH3:12])([CH3:11])[CH3:10].C([O-])([O-])=O.[K+].[K+].CCN(C(C)C)C(C)C>CC1C=CC=CC=1C.CCOC(C)=O.O>[C:9]([O:13][C:14]([N:16]1[CH2:21][C@H:20]2[C@H:18]([CH2:19]2)[C@H:17]1[CH2:22][NH:23][C:5]1[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 140 °C
Procedure
5-Bromo-2-chloro-pyrimidine (18.4 mmol) is added to a solution of (1S,2S,5R)-2-aminomethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (14.1 mmol) in o-xylene (30 mL). K2CO3 (42.4 mmol) and DIPEA (42.4 mmol) are added successively and the mixture is heated to 140° C. for 17 h. The mixture is cooled to RT and diluted with EtOAc (100 mL) and water (100 mL). The layers are separated and the aq. layer is extracted with DCM (100 mL). The combined organic layers are dried over MgSO4 and concentrated in vacuo. The obtained brownish solid is stirred in ether (75 mL). The suspension is filtered and washed with ether (25 mL) and the residue is dried in vacuo to give the desired product.
Workup
- temperatureThe mixture is cooled to RT
- customThe layers are separated
- extractionthe aq. layer is extracted with DCM (100 mL)
- dry with materialThe combined organic layers are dried over MgSO4
- concentrationconcentrated in vacuo
- filtrationThe suspension is filtered
- washwashed with ether (25 mL)
- customthe residue is dried in vacuo
Sources & evidence
- ORD record
- ord-4ef632e3b9b7411e90c7c9c26ee59a42
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063099B2
Reaction notes
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