Acetonitrile → HCID 58138307, compound

Temperature

65 °C

A 25 mL screw-top vial was charged with 4-amino-5-fluoropyrimidin-2-ol (99.7 mg, 0.772 mmol) and CH3CN (3 mL). BSA (0.284 mL, 1.16 mmol) was added, the vial was capped and the resulting heterogenous mixture was agitated on a rotary shaker at 65° C. for 80 min. The resulting clear and colorless solution was cooled to room temperature. O-Phenyl carbonochloridothioate (0.118 mL, 0.853 mmol) was added, and the reaction was agitated on a rotary shaker at 65° C. for 15 h. After cooling to room temperature, the crude material was diluted with CH2Cl2 (100 mL) and washed with saturated aqueous sodium chloride (satd aq NaCl) solution (50 mL×2). The organic solution was then dried over Na2SO4, filtered, and concentrated in vacuo. The green/brown residue was then purified by normal phase chromatography (gradient, 0 to 35% methyl alcohol (MeOH)/CH2Cl2) to afford O-phenyl 4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carbothioate (60.7 mg, 30%) as an 85% pure brown solid: mp 113-116° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 1H), 8.44 (d, J=7.2 Hz, 1H), 8.28 (s, 1H), 7.56-7.48 (m, 2H), 7.40-7.33 (m, 1H), 7.27-7.21 (m, 2H); ESIMS m/z 266 ([M+H]+).

1. additionBSA (0.284 mL, 1.16 mmol) was added
2. customthe vial was capped
3. temperatureThe resulting clear and colorless solution was cooled to room temperature
4. stirringthe reaction was agitated on a rotary shaker at 65° C. for 15 h
5. temperatureAfter cooling to room temperature
6. washwashed with saturated aqueous sodium chloride (satd aq NaCl) solution (50 mL×2)
7. dry with materialThe organic solution was then dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe green/brown residue was then purified by normal phase chromatography (gradient, 0 to 35% methyl alcohol (MeOH)/CH2Cl2)

ORD record

ord-d1f4ebec010448c8b9f481a36bd1c8f0

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318758B2