Phosphorus tribromide → 4-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

HRID 390804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390804
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11]O)=[CH:8][C:6]=2[N:7]=1.P(Br)(Br)[Br:20]>C1C=CC=CC=1>[Br:20][CH2:11][C:9]1[S:10][C:5]2[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:3][C:2]([Cl:1])=[N:7][C:6]=2[CH:8]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 46180605(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol

Produkt 1

HCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanol 29 (100 mg, 0.4 mmol) in benzene (3.0 mL) at 0° C. was added PBr3 (30 μl, 0.4 mmol). The reaction was heated at reflux for 1 hour. After cooling to room temperature the reaction was quenched by the addition of water. The aqueous layer was extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo. The crude product 30 did not require further purification (115 mg, 94%). MS (Q1) 350 (M)+

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. customwas quenched by the addition of water
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurification (115 mg, 94%)

Quellen und Nachweise

ORD-Eintrag
ord-1560cc2b14154b2d9882a60efdb936f2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383620B2

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