Potassium Persulfate → Methyl 6-cyclopropyl-2-(methylsulfonyl)pyrimidine-4-carboxylate

HRID 1748191

Reaktionsgleichung

Reaktionsgleichung von HRID 1748191
[CH:1]1([C:4]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[N:7]=[C:6]([C:14]([OH:16])=[O:15])[CH:5]=2)[CH2:3][CH2:2]1.[CH:17]1(C2N=C(SC)N=C(C(O)=O)C=2)CC1.OOS([O-])=O.[K+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].OS([O-])(=O)=O.[K+].CSC1N=CC=CN=1>O.C(#N)C>[CH:1]1([C:4]2[N:9]=[C:8]([S:10]([CH3:13])(=[O:11])=[O:12])[N:7]=[C:6]([C:14]([O:16][CH3:17])=[O:15])[CH:5]=2)[CH2:2][CH2:3]1

Komponenten

9

Edukt 6

HCID 24412Potassium PersulfateHCID 516920Potassium bisulfateHCID 5227722-(Methylsulfanyl)pyrimidineHCID 23707502Potassium hydroxy sulfite2×HCID 398708416-Cyclopropyl-2-(methylsulfanyl)pyrimidine-4-carboxylic acidHCID 679834126-Cyclopropyl-2-(methylsulfonyl)pyrimidine-4-carboxylic acid

Produkt 1

HCID 67983976Methyl 6-cyclopropyl-2-(methylsulfonyl)pyrimidine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

6-cyclopropyl-2-(methylsulfonyl)pyrimidine-4-carboxylic acid (I-20A). Into a 40 mL vessel was added 6-cyclopropyl-2-(methylthio)pyrimidine-4-carboxylic acid_(commerically available, Enamine Ltd, catalog number EN300-422464, 250 mg, 1.19 mmol) and acetonitrile (12.5 mL). This resulting solution was then added dropwise at RT over 5 min. to a separate 40 mL reaction vessel that was charged with a rapidly stirred suspension of Oxone™ (using Aldrich supplied Oxone which is a multicomponent triple salt mixture containing potassium monopersulfate, 2 KHSOs5.KHSO4.K2SO4, 2.50 g, 4.10 mmol) and water (15 mL). Upon complete addition of the methyl thiopyrimidine, the resulting suspension was heated to 65° C. for 20 min. and subsequently cooled to RT. The resulting yellow suspension was extracted with ethyl acetate (4×100 mL) and the organic extracts were dried over magnesium sulfate, filtered and concentrated to furnish the methyl sulfonyl pyrimidine as a residue that was used directly in the next step without isolation. MS m/z 243.1 (M+1).

Aufarbeitung

  1. additionThis resulting solution was then added dropwise at RT over 5 min. to a separate 40 mL reaction vessel that
  2. temperaturesubsequently cooled to RT
  3. extractionThe resulting yellow suspension was extracted with ethyl acetate (4×100 mL)
  4. dry with materialthe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa3dd2f3bcc74a7c85557b224e553005
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150568B2

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