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Hydrochloric Acid → n2-[4-(Dimethylphosphoryl)-2-methoxyphenyl]-n4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamine

HRID 921300
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 921300
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:5]=[CH:4][N:3]=1.[CH3:21][P:22]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[C:27]([O:32][CH3:33])[CH:26]=1)([CH3:24])=[O:23].Cl>COCCO>[CH3:24][P:22]([C:25]1[CH:31]=[CH:30][C:28]([NH:29][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:5]=[CH:4][N:3]=2)=[C:27]([O:32][CH3:33])[CH:26]=1)([CH3:21])=[O:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 67052699(4-Amino-3-methoxyphenyl)dimethylphosphine oxideHCID 866687912-Chloro-N-(2-(isopropylsulfonyl)phenyl)pyrimidin-4-amine

Produkt 1

HCID 68165220n2-[4-(Dimethylphosphoryl)-2-methoxyphenyl]-n4-[2-(propan-2-ylsulfonyl)phenyl]pyrimidine-2,4-diamineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8019
2-Methoxyethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2-chloro-N-[2-(propan-2-ylsulfonyl)phenyl]-pyrimidin-4-amine (0.017 g, 0.054 mmol) in 0.5 mL of 2-methoxyethanol in a vial was added 4-(dimethylphosphoryl)-2-methyoxyaniline (0.010 g, 0.044 mmol) as the HCl salt. The vial was sealed and the reaction was heated at 90° C. for 16 h. The reaction was quenched with 1N NaOH solution and the solution extracted ethyl acetate. The organic layers were combined, washed with saturated sodium chloride solution, dried with sodium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane) to afford the desired compound (15 mg, 72% yield). MS/ES+: m/z=475.

Aufarbeitung

  1. customThe vial was sealed
  2. customThe reaction was quenched with 1N NaOH solution
  3. extractionthe solution extracted ethyl acetate
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (0-10% 7N ammonia in methanol:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0d28e4c128d94da8b009f64ff0600c5a
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273077B2

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