4-Chloro-2-methylthiopyrimidine → 1-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

HRID 1785464

Reaktionsgleichung

Reaktionsgleichung von HRID 1785464
[C:1]1([C:7]2[CH:8]=[C:9]3[NH:14][CH2:13][CH2:12][CH2:11][N:10]3[C:15](=[O:17])[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Cl[C:71]1[CH:76]=[CH:75][N:74]=[C:73]([S:77][CH3:78])[N:72]=1>C1(C)C=CC=CC=1>[CH3:78][S:77][C:73]1[N:74]=[C:75]([N:14]2[CH2:13][CH2:12][CH2:11][N:10]3[C:15](=[O:17])[CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=[C:9]23)[CH:76]=[CH:71][N:72]=1

Komponenten

6

Edukt 4

HCID 971134-Chloro-2-methylthiopyrimidineHCID 634876Binap, (A+-)-HCID 125016018-Phenyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-6-oneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 575931211-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixture of 8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one (1.86 g, 8.23 mmol), sodium tert-butoxide (1.6 g, 16 mmol), BINAP (0.15 g, 0.207 mmol), and Pd (OAc)2 (55 mg, 0.2 mmol) was added toluene (20 mL) and 4-chloro -2-methylthiopyrimidine (1.5 mL, 12 mmol). After purged with N2 for 10 min, the overall mixture was heated at 70° C. for 3 h prior to being cooled to room temperature. The resulting material was diluted with saturated NHCl(aq), water, and DCM. The organic layer was taken and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtrated, and concentrated. Column chromatographic purification (3% MeOH in DCM) of the crude residue afforded the title compound as a yellow solid. MS m/e 351 (M+H)+.

Aufarbeitung

  1. customAfter purged with N2 for 10 min
  2. temperatureto being cooled to room temperature
  3. additionThe resulting material was diluted with saturated NHCl(aq), water, and DCM
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customColumn chromatographic purification (3% MeOH in DCM) of the crude residue

Quellen und Nachweise

ORD-Eintrag
ord-4adc0ba0538a4090bb0ebdd5cc78d520
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504403B2

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