Water → 6-(Bromomethyl)thieno[3,2-b]pyrazine

HRID 1184860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184860
[N:1]1[CH:6]=[CH:5][N:4]=[C:3]2[S:7][C:8]([CH2:10]O)=[CH:9][C:2]=12.P(Br)(Br)[Br:13].O.[OH-].[Na+]>C(Cl)Cl.C1COCC1>[Br:13][CH2:10][C:8]1[S:7][C:3]2[C:2](=[N:1][CH:6]=[CH:5][N:4]=2)[CH:9]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24614Phosphorus tribromideHCID 67125540Thieno[2,3-b]pyrazin-6-ylmethanol

Produkt 1

HCID 671255506-(Bromomethyl)thieno[3,2-b]pyrazineAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of thieno[3,2-b]pyrazin-6-ylmethanol 87 (408 mg, 2.455 mmol) in CH2Cl2 (8 mL) and THF (8 mL) was added phosphorus tribromide (1/166 mL, 12.27 mmol) and stirred overnight at rt. Water was added, alkalized with 2N NaOH and extracted with EtOAc. Organic layer was washed with NaHCO3 (aq) solution, brine, dried and evaporated. Purification by chromatography (CH2CL2) gave pure 6-(bromomethyl)thieno[3,2-b]pyrazine 47 (356 mg, 63%). NMR (400 MHz, CDCl3) 4.80 (s, 2H), 7.71 (s, 1H), 8.49 (d, J=2.3 Hz, 1H), 8.64 (d, J=2.3 Hz, 1H). (m/z)=229 and 231 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washOrganic layer was washed with NaHCO3 (aq) solution, brine
  3. customdried
  4. customevaporated
  5. customPurification by chromatography (CH2CL2)

Quellen und Nachweise

ORD-Eintrag
ord-41b48f1c844b4fc88f92fdcaca56d5da
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669256B2

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