Cesium carbonate → HCID 69929269, compound

HRID 869292Notes

Reaction equation

Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([OH:10])=[CH:4][N:3]=1.[C:11]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:11]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]=[CH:15][CH:14]=[C:13]([C:2]2[N:7]([CH3:8])[C:6](=[O:9])[C:5]([OH:10])=[CH:4][N:3]=2)[CH:12]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 40 mg (0.249 mmol) 2-chloro-5-hydroxy-3-methylpyrimidin-4(3H)-one in 1 ml THF was added 20.3 mg (0.025 mmol) 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane adduct, 74 mg (0.374 mmol) biphenyl-3-boronic acid, and 0.747 ml (0.747 mmol) 1 M aq Cs2CO3. The reaction mixture was heated to 120° C. for 20 min in the microwave, then diluted with 2 ml water, extracted with 10 ml EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by HPLC gave 10 mg (14% yield) of 2-biphenyl-3-yl-5-hydroxy-3-methylpyrimidin-4(3H)-one. 1H NMR δ (ppm) (CH3OH-d4): 7.83-7.77 (2H, m), 7.67 (2H, d, J=7.69 Hz), 7.64-7.55 (2H, m), 7.53-7.42 (3H, m), 7.37 (1H, t, J=7.33 Hz), 3.50 (3H, s). HRMS (ESI positive) calc (M+H)+=279.1128 found 279.1127.

Workup

extractionextracted with 10 ml EtOAc
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by HPLC

Sources & evidence

ORD record: ord-44c96e74b1ce4b1fada3200dbf5971c7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969364B2

Reaction notes

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