Iodine → 2-(methylsulfanyl)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1062316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062316
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]([S:12][CH3:13])[N:5]=1)[CH3:2].C(O[C:17](=[O:29])[CH2:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[CH:20]=1)C.N12CCCN=C1CCCCC2.II>C(OCC)(=O)C.CCCCCCC>[CH3:13][S:12][C:6]1[N:7]=[CH:8][C:9]2[CH:10]=[C:18]([C:19]3[CH:20]=[C:21]([O:27][CH3:28])[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=3)[C:17](=[O:29])[N:3]([CH2:1][CH3:2])[C:4]=2[N:5]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 107504444-(Ethylamino)-2-(methylthio)pyrimidine-5-carbaldehyde2×HCID 11831071Ethyl 2-(3,5-dimethoxyphenyl)acetate

Produkt 1

HCID 111991132-(methylsulfanyl)-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-oneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 8900HeptaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 5-L round bottomed flask was charged with 516 g (2.62 mol) of 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde, 587 g (2.62 mol) of (3,5-dimethoxy-phenyl)-acetic acid ethyl ester, and 391 mL (2.62 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was heated at 80° C. for one hour. Thin layer chromatography (TLC) (silica, 6:4/heptane:ethyl acetate, developed in an iodine chamber) showed all the 4-ethylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde was consumed. Ethyl alcohol (absolute, 2.75 L) was added to the reaction vessel, and the reaction mixture was cooled to room temperature. The solid that precipitated was collected by filtration, washed once with ethyl alcohol, and dried in a vacuum oven at 45° C. for 12 hours to provide 530 g (57% yield) of 2-methylsulfanyl-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidine-7-one. Proton NMR (DMSO) is consistent with the structure: 1H NMR (DMSO): δ 8.86 (s, 1H), 8.10 (s, 1H), 6.83 (d, 2H), 6.51 (s, 1H), 4.36 (q, 2H), 3.75 (s, 1H), 2.58 (s, 3H), 1.22 (t, 3H). The combined mother liquor and washes were allowed to stand at room temperature for seven days. At this time a second crop of precipitate was collected, washed once with ethyl alcohol, and dried in a vacuum oven at 45° C. for 12 hours to provide 79 g (8.5% yield) of 2-methylsulfanyl-6-(3,5-dimethoxyphenyl)-8-ethyl-8H-pyrido[2,3-d]pyrimidine-7-one. Proton NMR (DMSO) is consistent with the structure.

Aufarbeitung

  1. customwas consumed
  2. additionEthyl alcohol (absolute, 2.75 L) was added to the reaction vessel
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customThe solid that precipitated
  5. filtrationwas collected by filtration
  6. washwashed once with ethyl alcohol
  7. customdried in a vacuum oven at 45° C. for 12 hours

Quellen und Nachweise

ORD-Eintrag
ord-d7b1d8e6c2d945289cb693ba6f9c3bf2
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960662B2

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