Potassium Carbonate → 2,5-dichloro-N-(3-iodo-4-methoxyphenyl)pyrimidin-4-amine

HRID 541905

Reaktionsgleichung

Reaktionsgleichung von HRID 541905
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[NH2:5].[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([Cl:19])=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[N:17]=[C:16]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:2]([I:1])[CH:3]=2)[C:15]([Cl:19])=[CH:14][N:13]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 220545963-Iodo-4-methoxyaniline

Produkt 1

HCID 579618942,5-dichloro-N-(3-iodo-4-methoxyphenyl)pyrimidin-4-amineAusbeute 120,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 3-iodo-4-methoxyaniline (8.0 g, 0.021 mol) and 2,4,5-trichloropyrimidine (4.13 g, 0.0225 mol) in N,N-dimethylformamide (57 mL) was added potassium carbonate (7.40 g, 0.0536 mol). The resultant mixture was stirred overnight at room temperature. The reaction mixture was filtered to remove K2CO3 and concentrated to give the residue (10 grams). The residue was triturated with EtOAc, and filtered under vacuum. The residue was purified by silica gel column chromatography to give the desired product (2.54 g, 30%). LCMS for C11H9Cl21N3O (M+H)+: m/z=396.0, 398.0.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customto remove K2CO3
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0e0f0b6938264464b5917390d75944aa
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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