Diethylamine → HCID 178464354, compound

Temperature

80 °C

A 25 mL screw-top vial was charged with (E)-N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformimidamide (99.7 mg, 0.541 mmol), CH3CN (5 mL) and BSA (0.0665 mL, 0.272 mmol). The resulting mixture was then agitated on a rotary shaker at 80° C. for 19 h. After cooling to room temperature, thiophosgene (0.0415 mL, 0.544 mmol) was added, and the reaction mixture was agitated at room temperature on a rotary shaker for 90 min. At this time, diethylamine (0.112 mL, 1.08 mmol) was added, and the reaction mixture was further agitated at room temperature for 1 h. The heterogenous mixture was poured into a fritted funnel, and the resulting filtrate was concentrated in vacuo. This crude material was then purified by normal phase chromatography (gradient, 0 to 100% EtOAc/Hexane) to afford (E)-4-((dimethylamino)methyleneamino)-N,N-diethyl-5-fluoro-2-oxopyrimidine-1(2H)-carbothioamide (25.9 mg, 16%) as a pale yellow solid: mp 118-123° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.41 (d, J=3.2 Hz, 1H), 3.20 (s, 3H), 3.34 (q, J=6.7 Hz, 4H), 3.09 (s, 3H), 1.17 (s, 3H), 1.08 (s, 3H); ESIMS m/z 300 ([M+H]+).

1. temperatureAfter cooling to room temperature
2. stirringthe reaction mixture was agitated at room temperature on a rotary shaker for 90 min
3. stirringthe reaction mixture was further agitated at room temperature for 1 h
4. additionThe heterogenous mixture was poured into a fritted funnel
5. concentrationthe resulting filtrate was concentrated in vacuo
6. customThis crude material was then purified by normal phase chromatography (gradient, 0 to 100% EtOAc/Hexane)

ORD record

ord-3a4417170b564eff85a32055243877c4

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000002B2