Isopropyl chloroformate → HCID 58138312, compound

HRID 1880199Notes

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][CH:14]([CH3:16])[CH3:15])=[O:12]>>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])[C:4](=[O:9])[N:3]=1

Participants

Reactant 2

HCID 7917Isopropyl chloroformate

HCID 178509007HCID 178509007, compound

Product 1

HCID 58138312HCID 58138312, compoundYield 55%

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 isopropyl chloroformate (1 M solution in toluene; 2.9 mL, 2.9 mmol) were reacted, and the resulting material was purified via reverse phase chromatography (gradient, CH3CN/H2O) to give isopropyl 4-amino-5-fluoro-2-oxopyrimidine-1(2H)-carboxylate (0.225 g, 55%) as a white solid: mp 217-219° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.02-7.99 (m, 2H), 4.97 (septet, J=6.26 Hz, 1H), 1.28 (d, J=6.26 Hz, 6H); ESIMS m/z 216 ([M+H]+).

Workup

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

Sources & evidence

ORD record: ord-cfd7935590e7481fa3378a64299a60da
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318758B2

Reaction notes

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