Sodium hydride → (S)-N-(3-ethynylphenyl)-6-nitro-7-(tetrahydrofuran-3-yloxy)quinazolin-4-amine

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Reaction Steps

In an ice bath, NaH (1.87 g, 60%, 0.046 mol) was carefully added into a solution of (S)-tetrahydrofuran-3-ol (3.43 g, 0.039 mmol) in 100 mL anhydrous THF, and stirred for 2 hours at room temperature. Then N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine (10 g, 0.032 mol) was added and stirred for at 60° C. overnight. The solution was quenched with 1 mL H2O and concentrated, the residue was purified by silica gel column to give (S)—N-(3-ethynylphenyl)-6-nitro-7-(tetrahydrofuran-3-yloxy)quinazolin-4-amine as yellow solid 7.1 g (58.1% yield).

Provenance & Evidence