Triethylamine → 5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine

HRID 421996

Reaktionsgleichung

Reaktionsgleichung von HRID 421996
Cl[C:2]1[C:7]([I:8])=[C:6]([CH3:9])[N:5]=[C:4]([NH2:10])[N:3]=1.C(N(CC)CC)C.Cl.[NH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CCO.O>[I:8][C:7]1[C:2]([NH:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]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 441186934-Aminotetrahydropyran hydrochloride

Produkt 1

HCID 592727355-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamineAusbeute 51,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 4-chloro-5-iodo-6-methylpyrimidin-2-amine (16.0 g, 59.3 mmol) in EtOH (200 mL) and H2O (250 mL) was added triethylamine (30.0 mL, 207.5 mmol) and 4-aminotetrahydropyran HCl salt (9.75 g, 71.2 mmol) successively. The reaction was heated to reflux, stirred for 72 h, and then cooled to RT. About 80% of the solvent was evaporated under reduced pressure. The mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude product. The product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate) to afford 5-iodo-6-methyl-N4-(tetrahydro-2H-pyran-4-yl)pyrimidine-2,4-diamine as a light yellow crystal (yield: 10.23 g, 51.7%). LC/MS: calculated for C10H15IN4O (334.03). found: 335.08 (MH+). HPLC analytical purity: >99.0%.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customAbout 80% of the solvent was evaporated under reduced pressure
  4. customThe mixture was partitioned between ethyl acetate and H2O
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford the crude product
  8. customThe product was purified by a flash chromatography (50% ethyl acetate/hexanes to 100% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2ca2efa525ca4b29b8ac6868fb6fd18a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101622B2

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