Dichloromethane → (R)-8-Acetyl-2-(1-amino-ethyl)-3-(4-ethoxy-phenyl)-5,6,7,8-tetrahydro-3H-pyrido[2,3-d]pyrimidin-4-one

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Reaction Steps

D3 (268 mg, 0.59 mmol) was dissolved in 1:1 trifluoroacetic acid:dichloromethane (10 mL). The reaction stirred at room temperature for 30 min. The solvent was removed in vacuo, then 10% aqueous ammonium hydroxide was added until the aqueous pH=9. The aqueous layer was extracted three times with dichloromethane, then the combined organic layer was washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, and concentrated in vacuo, recovering 170 mg of D4. MS (MH+): 357.1. 1H NMR (400 MHz; CDCl3; T=298 K): δ 7.13 (ddd, 2H, J=18.9, 1.4, 1.1 Hz), 7.02 (ddd, 2H, J=9.0, 1.2, 0.8 Hz), 4.09 (dq, 2H, J=6.9, 1.2 Hz), 3.98-3.80 (ddq, 2H, J=62.6, 5.3, 1.0 Hz), 3.73 (dd, 1H, J=6.6, 1.2 Hz), 2.60 (s, 3H), 1.92 (m, 2H), 1.82 (broad s, 2H), 1.45 (ddd, 3H, J=8.3, 6.1, 1.3 Hz), 1.28-1.21 (m, 5H) ppm.

Provenance & Evidence