Hydrogen Bromide → 5-(3-fluoro-4-hydroxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one

HRID 1993347

Reaktionsgleichung

Reaktionsgleichung von HRID 1993347
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11](=[O:19])[N:12]([CH3:18])[C:13]([S:16][CH3:17])=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.Br.C([O-])(O)=O.[Na+].[OH-].[Na+]>CC(O)=O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11](=[O:19])[N:12]([CH3:18])[C:13]([S:16][CH3:17])=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

7

Edukt 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate3×HCID 588288915-(3-fluoro-4-methoxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one

Produkt 1

HCID 684206105-(3-fluoro-4-hydroxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

5-(3-Fluoro-4-methoxyphenyl)-3-methyl-2-methylthio-3H-pyrimidin-4-one (Step 4, 10.05 g, 35.85 mmol) was suspended in glacial HOAc (60 mL) and HBr (240 mL, 48%) was added. The reaction was put in an oil bath (110° C.) and stirred for 1.5 h. The reaction was heated to 120° C. and stirred for an additional 1.5 h, and which time LCMS showed very little starting material. The reaction was cooled to 0° C., and EtOAc (300 mL) was added. Saturated NaHCO3 (0.2 L) was added, the reaction was transferred to a 2 L Erlenmeyer flask, and 0.83 L saturated NaHCO3 was added. The reaction was stirred overnight, then more NaHCO3 (300 mL) and 5 N NaOH (100 mL) was added, and the reaction was stirred for 30 min then filtered. The solid was collected while the pH of the filtrate was adjusted to about 5 using 5 N NaOH and filtered again. The solid from both filtrations was combined and dried in vacuo to give title compound. MS (ESI pos. ion) m/z: 267. Calc'd for C12H11FN2O2S Mol. Wt.: 266.05.

Aufarbeitung

  1. customThe reaction was put in an oil bath
  2. temperatureThe reaction was heated to 120° C.
  3. stirringstirred for an additional 1.5 h
  4. temperatureThe reaction was cooled to 0° C.
  5. additionwas added
  6. stirringThe reaction was stirred overnight
  7. stirringthe reaction was stirred for 30 min
  8. filtrationthen filtered
  9. customThe solid was collected while the pH of the filtrate
  10. filtrationfiltered again
  11. filtrationThe solid from both filtrations
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ba69af8f5a4d4772b1860e779c272d1e
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652009B2

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