Triethylamine → 8-((4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)ethynyl)-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 920324

Reaktionsgleichung

Reaktionsgleichung von HRID 920324
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]#[CH:23])=[CH:18][CH:17]=2)=[CH:11][C:10]=1[C:24]([F:27])([F:26])[F:25].Cl[C:29]1[CH:39]=[C:33]2[N:34]([CH3:38])[CH2:35][CH2:36][CH2:37][N:32]2[C:31](=[O:40])[N:30]=1>C1COCC1.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]#[C:23][C:29]3[CH:39]=[C:33]4[N:34]([CH3:38])[CH2:35][CH2:36][CH2:37][N:32]4[C:31](=[O:40])[N:30]=3)=[CH:20][CH:21]=2)=[CH:11][C:10]=1[C:24]([F:25])([F:26])[F:27]

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-oneHCID 866763761-Chloro-4-(4-ethynylphenoxy)-2-(trifluoromethyl)benzene

Produkt 1

HCID 712365888-((4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)ethynyl)-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-oneAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of bis(triphenylphosphine)palladium(II) chloride (70.3 mg, 0.1 mmol) and copper(I) iodide (19.1 mg, 0.1 mmol) in anhydrous THF (12 mL), was purged with Ar for 10 mins at rt. The suspension was treated with triethylamine (0.42 mL, 3.0 mmol), and 1-chloro-4-(4-ethynylphenoxy)-2-(trifluoromethyl)benzene (446 mg, 1.5 mmol) was added under an Ar atmosphere, which produced a dark amber color. After 5 mins, 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (100 mg, 0.5 mmol) was added, and stirred for 2 h at 50° C. The reaction mixture was diluted with EtOAc, washed with water, and then concentrated. The residue was purified by MDAP to afford the title compound (30 mg) as a pale yellow solid.

Aufarbeitung

  1. customwas purged with Ar for 10 mins at rt
  2. additionwas added under an Ar atmosphere, which
  3. customproduced a dark amber color
  4. washwashed with water
  5. concentrationconcentrated
  6. customThe residue was purified by MDAP

Quellen und Nachweise

ORD-Eintrag
ord-a660d1c907364c4685d67b3c06e8e494
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273054B2

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