Sodium Hydroxide → HCID 131734517, compound

Participants

Reaction Steps

To a suspension of ((5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonyl)phosphoramidic acid (2) (0.030 g, 0.054 mmol) in ethanol (3 mL) was added NaOH (6.40 mg, 0.161 mmol) in 0.500 mL of water. The reaction mixture was stirred under nitrogen atmosphere at room temperature for 2 h. The reaction mixture was concentrated to dryness and the residue washed with ethyl acetate (2×8 mL), acetone (2×8 mL) and acetonitrile (2×8 mL) to afford trisodium (5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)quinazolin-2-yl)pyridin-3-yl)sulfonylphosphoramidate (3) (0.028 g, 0.046 mmol, 85% yield) as a pink solid. 1H NMR (400 MHz, deuterium oxide) δ (ppm) 4.54 (s, 2H), 7.11 (d, J=7.78 Hz, 1H), 7.18-7.26 (m, 2H), 7.28-7.41 (m, 5H), 7.61-7.79 (m, 3H), 8.28 (d, J=4.52 Hz, 1H), 8.89-8.95 (m, 1H), 9.08 (d, J=2.01 Hz, 1H), 9.20 (d, J=1.76 Hz, 1H); LCMS Method D: retention time 1.24 min, [M+l]=469. HPLC Method C: Purity 95.1%, retention time 6.18 min, HPLC Method E: Purity 94.0%, retention time 12.16 min. Elemental Analysis: Compound was hygroscopic and accurate EA not obtained.

Provenance & Evidence