Triethylamine → (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine

HRID 421999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421999
Cl[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.Cl.[O:12]1[CH2:16][CH2:15][C@@H:14]([NH2:17])[CH2:13]1.C(N(CC)CC)C>CCO.O>[I:8][C:7]1[C:2]([NH:17][C@@H:14]2[CH2:15][CH2:16][O:12][CH2:13]2)=[N:3][C:4]([NH2:10])=[N:5][C:6]=1[CH3:9]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 116447204-Chloro-5-iodo-6-methylpyrimidin-2-amineHCID 46856371(3R)-3-Aminotetrahydrofuran hydrochloride

Produkt 1

HCID 59272736(R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamineAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (7.03 g, 26.08 mmol), (R)-tetrahydrofuran-3-amine hydrochloride (Milestone PharmTech, 3.90 g, 31.3 mmol) and triethylamine (9.236 g, 91.3 mmol) in EtOH (150 mL) and water (50 mL) was refluxed for 2-3 days. The reaction was monitored by LC/MS. After completion, the reaction mixture was cooled to ambient temperature and partitioned between 150 mL of ethyl acetate and 200 mL of water. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate afforded (R)-5-iodo-6-methyl-N4-(tetrahydrofuran-3-yl)pyrimidine-2,4-diamine (4.53 g, 54% yield). MS (EI) for C9H13IN4O: 321.0 (MH+).

Aufarbeitung

  1. temperaturewas refluxed for 2-3 days
  2. custompartitioned between 150 mL of ethyl acetate and 200 mL of water
  3. extractionThe aqueous layer was extracted by ethyl acetate 3 times
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization of the residue from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-51c629c0ed884ffa986947f9f35853ef
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101622B2

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