Ethyl Acetate → 5-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

HRID 875942

Reaktionsgleichung

Reaktionsgleichung von HRID 875942
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[O:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>O1CCOCC1>[Br:1][C:2]1[C:3]([NH:16][CH:13]2[CH2:14][CH2:15][O:10][CH2:11][CH2:12]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 4192234-Aminotetrahydropyran

Produkt 1

HCID 595508905-Bromo-2-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amineAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

5-Bromo-2,4-dichloropyrimidine (5.0 g, 21.9 mmol), tetrahydro-2H-pyran-4-amine (2.22 g, 21.9 mmol), and N-ethyl-N-isopropylpropan-2-amine (4.25 g, 32.9 mmol) were dissolved in dioxane (50 ml) and the reaction was stirred at room temperature for 12 hours. Ethyl acetate was added to the reaction mixture and the organic layer was washed with water and brine. The organic layer was dried with sodium sulfate. Removal of solvent gave (5-bromo-2-chloro-pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine (32) as a light yellow solid (6.75 g, 99%). 1H NMR (500 MHz, CD3OD) δ ppm 8.04 (1 H, s), 4.14-4.21 (1 H, m), 3.89 (2 H, dd, J=11.4, 4.3 Hz) 3.43 (2 H, td, J=11.9, 2.0 Hz), 1.80 (2 H, ddd, J=12.6, 4.2, 1.8 Hz), 1.63 (2 H, qd, J=12.2, 4.5, Hz); LCMS-ESI (POS), M/Z, M+1: Found 292.0, Calculated 292.

Aufarbeitung

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. customRemoval of solvent

Quellen und Nachweise

ORD-Eintrag
ord-85091248ae344965ba2f9333eb73f4d4
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980903B2

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