2,4-Dichloro-5-pyrimidinecarboxylic acid → 2-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

HRID 645510

Reaktionsgleichung

Reaktionsgleichung von HRID 645510
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[CH2:18]1[C:20]2([CH2:25][CH2:24][CH:23]([CH2:26][OH:27])[CH2:22][CH2:21]2)[CH2:19]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([O:27][CH2:26][CH:23]2[CH2:24][CH2:25][C:20]3([CH2:18][CH2:19]3)[CH2:21][CH2:22]2)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acidHCID 23665647Potassium tert-butoxideHCID 53487089(Spiro(2.5)octan-6-yl)methanol

Produkt 1

HCID 866277982-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of a 2,4-dichloroprimidine-5-carboxylic acid (440 mg) in THF (4.0 mL) are added t-BuOK (potassium tert-butoxide) (5.7 mmol) and spiro[2.5]oct-6-ylmethanol (2.3 mmol) in THF (1.0 mL) at 0° C. After stirring at 0° C. for 1.5 h, the reaction is quenched by the addition of sat. aq. NaHCO3. The mixture is washed with ether. The aqueous layer is acidified to pH 2 with sat. aq. KHSO4, then extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude title compound.

Aufarbeitung

  1. customthe reaction is quenched by the addition of sat. aq. NaHCO3
  2. washThe mixture is washed with ether
  3. extractionextracted with AcOEt
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f7943dc509964b26b286896b26da78a5
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704996B2

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