Ethyl chloroformate → HCID 58138315, compound

HRID 1880198Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4](=[O:9])[N:3]=1

Participants

Reactant 2

HCID 10928Ethyl chloroformate

HCID 178509007HCID 178509007, compound

Product 1

HCID 58138315HCID 58138315, compoundYield 25.6%

Procedure

Using the procedure of Example 2, 4-amino-5-fluoro-pyrimidin-2-ol (0.25 g, 1.9 mmol), BSA (1.41 mL, 5.8 mmol) and ethyl chloroformate (0.277 mL, 2.9 mmol) were reacted, and the resulting material was purified via reverse phase chromatography (gradient, CH3CN/H2O) to give ethyl 4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.098 g, 25.6%) as a white solid: mp 190-193° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.29 (s, 1H), 8.04-8.01 (m, 2H), 4.27 (q, J=7.25 Hz, 2H), 1.26 (t, J=7.25 Hz, 3H); ESIMS m/z 200 ([M−H]−).

Workup

customwere reacted
customthe resulting material was purified via reverse phase chromatography (gradient, CH3CN/H2O)

Sources & evidence

ORD record: ord-3519b30540544454b53434c5e7331617
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318758B2

Reaction notes

Loading…