Potassium Phosphate, Tribasic → 2-Chloro-4-[(1E)-3-methoxy-1-propen-1-yl]pyrimidine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]([O:12][CH2:13][CH:14]=[CH:15]B1OC(C)(C)C(C)(C)O1)(=O)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CC1CCCO1.O.C([O-])(O)=O.[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:7]=[C:6](/[CH:15]=[CH:14]/[CH2:13][O:12][CH3:9])[CH:5]=[CH:4][N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 125 °C
Procedure
A microwave vessel was charged with 2,4-dichloropyrimidine (500 mg, 3.36 mmol), 3-acetoxy-1-propenylboronic acid pinacol ester (997 mg, 5.03 mmol) and solid potassium phosphate tribasic (2.14 g, 10.1 mmol), which were then suspended in 2-methyltetrahydrofuran (4 ml) and water (1 ml). The vessel was deoxygenated three times, then Palladium(II) acetate (37.7 mg, 0.17 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (138 mg, 0.34 mmol) were introduced and the dark mixture was heated under microwave irradiation at 125° C. for 15 min. The reaction mixture was diluted with saturated aqueous NaHCO3 (80 ml) and extracted with EtOAc (2×75 ml). The combined organic layers were dried over MgSO4 and concentrated. The crude orange oil was purified by flash column chromatography (SiO2: 100% Hex to 100% EtOAc), which afforded 2-chloro-4-[(1E)-3-methoxyprop-1-en-1-yl]pyrimidine (623 mg, 3.21 mmol, 96% yield) as an orange-red solid. MS ESI: [M+H]+ m/z 185.1.
Workup
- customThe vessel was deoxygenated three times
- extractionextracted with EtOAc (2×75 ml)
- dry with materialThe combined organic layers were dried over MgSO4
- concentrationconcentrated
- customThe crude orange oil was purified by flash column chromatography (SiO2: 100% Hex to 100% EtOAc), which
Sources & evidence
- ORD record
- ord-e8549b41c68747549c6c278d593fe8fa
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08551984B2
Reaction notes
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