Sodium Carbonate → HCID 58166641, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:17][CH2:16]1>O.[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]>[CH:16]([C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH2:1])[CH:7]=1)=[CH2:17]Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-amino-6-chloropyrimidine (2.5 g, 19.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride (810 mg, 1.2 mmol), sodium carbonate (8.14 g, 76.8 mmol) and vinyl borane pinacol ester (3.9 mL, 23 mmol) in dioxane (11.5 mL) and water (11.5 mL) under nitrogen, was heated at 100° C. for 20 hours then cooled to ambient temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-10% methanol in DCM) to afford the title compound as a yellow solid (1.87 g, 80% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.30 (s, 1H), 6.83 (s, 2H), 6.57 (dd, J=17.2, 10.5 Hz, 1H), 6.36 (s, 1H), 6.26 (dd, J=17.2, 2.1 Hz, 1H), 5.48 (dd, J=10.5, 2.1 Hz, 1H).
Workup
- temperaturethen cooled to ambient temperature
- customThe reaction mixture was partitioned between ethyl acetate and water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel flash chromatography (0-10% methanol in DCM)
Sources & evidence
- ORD record
- ord-c7e200e202b84383b191c607a4d157fc
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309240B2
Reaction notes
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