Thionyl Chloride → 2-{6-[3(R)-Amino-piperidin-1-yl]-5-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl}-benzonitrile

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Reaction Steps

Compound 4 (40 mg, 0.1 mmol) in CHCl3 (2 mL) was treated with SOCl2 (200 μL) at 100° C. for 30 min, concentrated, and then purified by LC-MS to give the title compound 7. 1H-NMR (400 MHz, CDCl3-CD3OD 10:1): δ 7.73 (d, J=7.6 Hz, 1 H), 7.64 (t, J=7.6 Hz, 1 H), 7.45 (t, J=7.6 Hz, 1 H), 7.14 (d, J=8.1 Hz, 1 H), 5.32-5.42 (m, 2 H), 3.43 (s, 3 H), 3.33-3.40 (m, 2 H), 3.17 (m, 2 H), 2.87 (s, 1 H), 2.08 (m, 1 H), 1.70 (m, 1 H), 1.32-1.43 (m, 2 H). MS (ES) [m+H] calc'd for C18H21ClN5O2, 374.1; found, 374.1.

Provenance & Evidence