Anisole → HCID 18691331, compound

Temperature

0 °C

Part A: Anisole (2.16 g), n-butyllithium (2.5 M in hexanes, 4.0 mL), and dry ether (4.0 mL) were stirred 18 h at room temperature. Ether (5 mL) and tetrahydrofuran (SmL) were added to make a 0.47 M solution of 2-methoxyphenyllithium (21.12 mL), of which 0.47 mL was added to 2-chloro-4-methylpyrimidine (0.71 g, prepared as described by Strekowski et al (J. Heterocylic Chem. 27, 1393 (1990)) dissolved in dry ether (37 mL) and stirred 30 minutes at -30° C. and 2 hours at 0° C. The reaction was quenched with acetic acid (515 μL), water (36 μL) and tetrahydrofuran (5 mL). 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (1.31 g) dissolved in tetrahydrofuran (5 mL) was added to the reaction which was then stirred 20 minutes. 1N Sodium hydroxide (aq.) (10 mL) was added at 0° C. and the reaction was washed with iN sodium hydroxide (3×10 mL). The organic layer was filtered through silica gel and concentrated to dryness to give 2-chloro-6-methyl-4-(2-methoxyphenyl)pyrimidine (0.72 g).

1. customprepared
2. customThe reaction was quenched with acetic acid (515 μL), water (36 μL) and tetrahydrofuran (5 mL)
3. dissolution2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (1.31 g) dissolved in tetrahydrofuran (5 mL)
4. additionwas added to the reaction which
5. stirringwas then stirred 20 minutes
6. addition1N Sodium hydroxide (aq.) (10 mL) was added at 0° C.
7. washthe reaction was washed with iN sodium hydroxide (3×10 mL)
8. filtrationThe organic layer was filtered through silica gel
9. concentrationconcentrated to dryness

ORD record

ord-8b6976539c524a5f926c4170f33eff8d

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06103737