Potassium Carbonate → 5-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amine

HRID 1853117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1853117
[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:18][CH2:17][C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)([CH3:20])[CH3:19])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 6006905-Bromo-2-fluoropyrimidineHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

Produkt 1

HCID 674528925-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 5-bromo-2-fluoropyrimidine (1.0 g, 5.6 mmol, 1.0 equiv) and 2-(4-fluorophenyl)-2-methylpropan-1-amine (1.05 g, 6.3 mmol. 1.1 equiv) in isopropanol (12 mL) in a microwave vial equipped with a stir bar was added potassium carbonate (3.68 g, 11.2 mmol, 2.0 equiv). The vial was fitted with a microwave vial cap and heated to 120° C. for 45 min. The reaction mixture was filtered to remove the solid potassium carbonate and concentrated in vacuo. After the residue was redissolved in EtOAc and water, the organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography (3%-5% MeOH/DCM) provided the title compound as a yellow solid (1.15 g, 65%), (m/z [M+H]=324.2).

Aufarbeitung

  1. customThe vial was fitted with a microwave
  2. customvial cap
  3. filtrationThe reaction mixture was filtered
  4. customto remove the solid potassium carbonate
  5. concentrationconcentrated in vacuo
  6. dissolutionAfter the residue was redissolved in EtOAc
  7. washwater, the organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification by silica gel chromatography (3%-5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-9dd61d3147e04ea79f93d79345ba3dc7
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962632B2

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