Ammonium Chloride → HCID 59639533, Verbindung

HRID 556585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 556585
C1[O:18][CH2:17][CH2:16]OCCOCCOCCOCCOC1.FC(F)(F)COP(CC(OC)=O)(=O)OCC(F)(F)F.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:48][C:49]1[C:54]([CH:55]=O)=[C:53]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[F:63])[N:52]=[C:51]([S:64][CH3:65])[N:50]=1.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1.CCOCC>[F:63][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=1[C:53]1[C:54]2[CH:55]=[CH:16][C:17](=[O:18])[NH:48][C:49]=2[N:50]=[C:51]([S:64][CH3:65])[N:52]=1

Komponenten

9

Edukt 5

HCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 184894Nsc 634137HCID 3251421Potassium bis(trimethylsilyl)amideHCID 9856557HCID 9856557, Verbindung

Produkt 1

HCID 59639533HCID 59639533, VerbindungAusbeute 108,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 18-crown-6 (422 mg, 1.6 mmol, 5 eq) and bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (81 uL, 0.38 mmol, 1.2 eq) in anhyd THF (20 mL) was cooled to −78°, potassium bis(trimethylsilyl)amide (0.96 mL, 0.48 mmol, 1.5 eq) as a 0.5 mol solution in toluene was added. This solution was stirred for additional 30 min at −78° and 4-amino-6-(2-fluoro-phenyl)-2-methylsulfanyl-pyrimidine-5-carbaldehyde (85 mg, 0.32 mmol) in dry THF (1 mL) was added dropwise. The reaction mixture was then stirred for 8 h at −78° and warmed to 23°, and stirred 16 h. Saturated aq NH4Cl (5 mL), followed by Et2O (20 mL), was added. The layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4), filtered and solvent was evaporated. The yellow residue was purified by Flash chromatography to afford 100 mg (91% yield) of 4-(2-fluoro-phenyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one. 1H-NMR δ 2.62 (s, 3H), 6.55 (d, 1H, J=9.9 Hz), 7.26 (m, 3H), 7.52 (m, 2H), 8.99 (br s, 1H). LC MS (m/e)=288 (MH+). Rt=1.75 min.

Aufarbeitung

  1. stirringThe reaction mixture was then stirred for 8 h at −78°
  2. temperaturewarmed to 23°
  3. stirringstirred 16 h
  4. additionwas added
  5. customThe layers were separated
  6. washThe organic layer was washed with satd aq NaCl
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customsolvent was evaporated
  10. customThe yellow residue was purified by Flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3311936772c64ceba86463e489b7dab1
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058282B2

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