Water → Isobutyl 4-(4-(2-(difluoromethyl)phenyl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 645459Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9]2)[N:3]=1.[F:21][CH:22]([F:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:21][CH:22]([F:38])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:10][CH2:9]2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of the isobutyl 4-(4-chloropyrimidin-2-yl)piperazine -1-carboxylate 8 and 2-(2-(difluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 11 (1.2 eq) in acetonitrile was added Pd(PPh3)4 (0.10 eq), K2CO3 (2 eq) and water. The vial was sealed and heated by microwave irradiation at 120° C. for 15 minutes. The solvent was evaporated and the residue was dissolved in DMF and purified by reverse phase HPLC. m/z 391.1 (M+1), r.t: 3.59.

Workup

customThe vial was sealed
customThe solvent was evaporated
dissolutionthe residue was dissolved in DMF
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-969907ce0dc44df083077f4a097acaae
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705002B2

Reaction notes

Loading…