N-Iodosuccinimide → N4-(Cyclopropylmethyl)-5-iodopyrimidine-2,4-diamine

HRID 875977

Reaktionsgleichung

Reaktionsgleichung von HRID 875977
[I:1]N1C(=O)CCC1=O.[CH:9]1([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[CH2:11][CH2:10]1>CC(O)=O>[CH:9]1([CH2:12][NH:13][C:14]2[C:19]([I:1])=[CH:18][N:17]=[C:16]([NH2:20])[N:15]=2)[CH2:10][CH2:11]1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 20277654N4-(cyclopropylmethyl)pyrimidine-2,4-diamine

Produkt 1

HCID 58299566N4-(Cyclopropylmethyl)-5-iodopyrimidine-2,4-diamineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-iodosuccinimide (11.5 g, 50.9 mmol) was added to a solution of compound 237 (7.60 g, 46.3 mmol) in AcOH (90 mL). The reaction was warmed to 80° C. and stirred for 1.5 h. Solvent was removed in vacuo. The residue was taken up in dichloromethane (200 mL) and water. The aqueous layer was brought to pH 12 with 5 N NaOH and organics were sequestered. The aqueous was extracted further with dichloromethane (2×100 mL). The combined organics were treated with solid sodium thiosulfate, dried with MgSO4 and concentrated in vacuo. Silica gel chromatography (gradient elution 10 to 75% ethyl acetate in hexanes) afforded compound 238 (8.0 g, 60% yield).

Aufarbeitung

  1. customSolvent was removed in vacuo
  2. extractionThe aqueous was extracted further with dichloromethane (2×100 mL)
  3. additionThe combined organics were treated with solid sodium thiosulfate
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography (gradient elution 10 to 75% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f1067da8d7604dfe8764f95885a2f7af
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980903B2

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