Sodium Carbonate → 6-(4-Amino-3,5-dimethylphenyl)-3-methylpyrimidin-4(3H)-one

HRID 237586

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=[C:5]([CH3:18])[C:3]=1[NH2:4].Cl[C:20]1[N:25]=[CH:24][N:23]([CH3:26])[C:22](=[O:27])[CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[NH2:4][C:3]1[C:5]([CH3:18])=[CH:6][C:7]([C:20]2[N:25]=[CH:24][N:23]([CH3:26])[C:22](=[O:27])[CH:21]=2)=[CH:8][C:2]=1[CH3:1]

Participants

Conditions

Temperature: 65 °C

Procedure

In a microwave vial 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.6 g) and 6-chloro-3-methylpyrimidin-4(3H)-one (3 g) are suspended in N,N-dimethylformamide (30 mL) and Na2CO3 (26 mL of a 2M aqueous solution). The mixture is purged for 5 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (508 mg) is added, the vial is sealed and the mixture is stirred at 65° C. for 12 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated to give the title compound. Yield: 2.6 g; LC (method 11): tR=0.71 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

Workup

customThe mixture is purged for 5 minutes with argon
addition[1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (508 mg) is added
customthe vial is sealed
temperatureAfter cooling to room temperature the mixture
customis Partitioned between water and ethyl acetate
extractionThe aqueous phase is extracted twice with ethyl acetate
washthe combined organic phases are washed with brine
dry with materialdried (MgSO4)
customThe solvents are evaporated

Sources & evidence

ORD record: ord-c31715c430bd41598881d2f21c3a7fac
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Linked notes

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