Phosphorus tribromide → 4-(2-(Bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine

HRID 1692749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692749
[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)=[N: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[N:8]=1

Komponenten

4

Edukt 2

HCID 24614Phosphorus tribromideHCID 57685397(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol

Produkt 1

HCID 576853964-(2-(Bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of (5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanol 56 (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 4-(2-(bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine 57 did not require further purification (x mg, x %). MS (Q1)×(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 (x mg, x %)

Quellen und Nachweise

ORD-Eintrag
ord-756d5ff211aa4788ae9bac31c4cce01b
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158626B2

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