Sodium Sulfate → HCID 59421275, compound

HRID 1036612Notes

Reaction equation

[O-:1]S([O-])(=O)=O.[Na+].[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[N:26][C:27]([S:30][CH3:31])=[N:28][CH:29]=1)=[O:23])[CH3:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])=[N:26][C:27]([S:30]([CH3:31])=[O:1])=[N:28][CH:29]=1)=[O:23])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A Na2SO4-dried solution of m-CPBA (10.64 g, ca. 45 mmol) in CH2Cl2 (100 mL) was added drop wise to a cold (−65° C.) solution of 4-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester in CH2Cl2 (200 mL) keeping the temperature below −65° C. The yellow suspension was allowed to warm to 0° C. over 1 hour. After 3 hours at 0° C., a saturated aqueous NaHCO3 solution (100 mL) was added to quench the reaction. The organic layer was separated, washed with saturated aqueous NaCl solution, dried over Na2SO4, and concentrated. The product was taken up in CH2Cl2 and washed again with a saturated aqueous NaHCO3 solution to remove traces of m-C(P)BA giving 4-(2-fluoro-phenyl)-2-methanesulfinyl-pyrimidine-5-carboxylic acid ethyl ester (12.86 g, >100%).

Workup

customthe temperature below −65° C
customto quench
customthe reaction
customThe organic layer was separated
washwashed with saturated aqueous NaCl solution
dry with materialdried over Na2SO4
concentrationconcentrated
washwashed again with a saturated aqueous NaHCO3 solution
customto remove traces

Sources & evidence

ORD record: ord-bd9fb57e2bcc420987036a1ce356fcb0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546414B2

Reaction notes

Loading…