D
T.-Y. Yang et al.
Letter
Synlett
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(23) Ethyl
4-Methyl-6-phenylpyrimidine-5-carboxylate
(3a);
Typical Procedure
An oven-dried tube was charged with ethyl 6-methyl-4-phenyl-
2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (1a; 0.276 g,
1 mmol), eosin B (2; 0.012 g, 0.02 mmol), and DMF (3 mL). The
stirred mixture was irradiated with a 15 W blue light for 12 h at
r.t., while the reaction was monitored by TLC. The reaction was
then quenched with sat. aq NH4Cl (3 mL) and the mixture was
extracted with EtOAc (3 × 15 mL). The organic layers were com-
bined, washed with brine, and dried (MgSO4). The crude
product was purified by column chromatography [silica gel, PE–
EtOAc (1:15)] to give a yellow oil; yield: 214 mg (0.88 mmol,
88%). 1H NMR (600 MHz, CDCl3): δ = 9.15 (s, 1 H), 7.65 (d, J = 7.6
Hz, 2 H), 7.46 (d, J = 7.4 Hz, 2 H), 4.20 (q, J = 7.2 Hz, 2 H), 2.63 (s,
3 H), 1.08 (t, J = 7.2 Hz, 3 H). 13C NMR (100 MHz, CDCl3): δ =
167.67, 164.95, 163.20, 158.06, 137.53, 130.13, 128.58, 128.26,
125.95, 61.93, 22.56, 13.62. HRMS (ESI+): m/z [M + H]+ calcd for
(11) Kim, S. S.; Choi, B. S.; Lee, J. H.; Lee, K. K.; Lee, T. H.; Kim, Y. H.;
Shin, H. Synlett 2009, 599.
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C
14H15N2O2: 243.1128; found: 243.1123.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–D