Bromine → 6-Bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine

HRID 886752

Reaktionsgleichung

Reaktionsgleichung von HRID 886752
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][C:9]2[N:10]=[CH:11][C:12]3[CH:17]=[CH:16][S:15][C:13]=3[N:14]=2)[CH2:3][CH2:2]1.[Br:18]Br>C(Cl)Cl>[Br:18][C:16]1[S:15][C:13]2[N:14]=[C:9]([CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[N:10]=[CH:11][C:12]=2[CH:17]=1

Komponenten

4

Edukt 2

HCID 24408BromineHCID 685591422-(2-Morpholinoethyl)thieno[2,3-d]pyrimidine

Produkt 1

HCID 685604506-Bromo-2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-(2-morpholinoethyl)thieno[2,3-d]pyrimidine (1.0 g, 3.79 mmol) in DCM (50 mL) at 0° C. was added a solution of bromine (1.2 eq) in DCM (3 mL) dropwise. The resulting solution was stirred at 0° C. for 30 min. The reaction mixture was quenched with saturated solution of NH4Cl. The layers were separated, and the aqueous layer was extracted with DCM (3×25 mL). Organic layers were combined, washed with brine (2×30 mL), dried over MgSO4, filtered and concentrated to provide the title compound (0.910 g). MS (ES+): 345 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated solution of NH4Cl
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (3×25 mL)
  4. washwashed with brine (2×30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4d9559c1b16448df8b0449c65bbd21ee
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247409B2

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