Sodium periodate → HCID 59432143, compound

HRID 245297Notes

Reaction equation

HRID 245297 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:11]=C)=[C:9]([NH2:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=1)=[O:4].I([O-])(=O)(=O)=[O:25].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH:11]=[O:25])=[C:9]([NH2:13])[N:8]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([O:21][CH3:22])[C:15]=2[F:23])[N:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 594321224-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenyl-6-methoxycarbonylpyrimidine

Product 1

HCID 59432143HCID 59432143, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid methyl ester (0.500 g, 1.5 mmol) was dissolved in THF (3 mL) and water (3 mL). Osmium tetroxide (4 mg, 0.015 mmol) was added and the reaction mixture was stirred for 2 min. Sodium periodate (0.63 g, 3 mmol) was then added over a period of 2 min. The reaction mixture was stirred for 16 h at ambient temperature then poured into water (150 mL) and extracted with dichloromethane thrice. The combined organic layers were dried, filtered and concentrated to afford the title compound (490 mg, 98% yield) in sufficient purity for subsequent reactions. An analytical sample was obtained by reverse phase chromatography: 1H NMR (CDCl3) δ 10.31 (s, 1H), 8.72 (br s, 1H), 7.77 (dd, 1H), 7.23 (m, 1H), 6.03 (br s, 1H), 4.06 (s, 3H), 4.01 (d, 3H).

Workup

  1. stirringThe reaction mixture was stirred for 16 h at ambient temperature
  2. extractionextracted with dichloromethane thrice
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd63535335cc45318f4cd3fa53cc7897
Source dataset
uspto-grants-2014_02
Patent number
US08658791B2

Reaction notes

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