1,2-Dichloroethane → 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 1805868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1805868
[CH2:1]([N:8]1[C:16]2[C:15]([Cl:17])=[N:14][C:13](N)=[N:12][C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=O.[Cl:26]CCCl>>[CH2:1]([N:8]1[C:16]2[C:15]([Cl:17])=[N:14][C:13]([Cl:26])=[N:12][C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 111,2-DichloroethaneHCID 10906Tert-Butyl nitriteHCID 576936175-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine

Produkt 1

HCID 147277655-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidineAusbeute 77 %

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

To a suspension of 5-benzyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-2-amine (641 mg, 2.5 mmol) in 1,2-dichloroethane (35 mL) was cooled to −10° C. SbCl3 (850 mg, 3.7 mmol) was added. The reaction mixture was stirred for 5 min. t-butyl nitrite (2.1 mL, 17.4 mmol) was added dropwise and the stirred mixture was from −10° C. to room temperature for 5 h. Upon completion of the reaction, the reaction mixture was poured into ice water and washed with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with Hexanes:Ethyl acetate (9:1-1:1), and gave the product as an off-white solid (528 mg, 77%).

Aufarbeitung

  1. additionwas added dropwise
  2. customUpon completion of the reaction
  3. washwashed with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluting with Hexanes:Ethyl acetate (9:1-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9af5055370b14c76b7b05d544f9418a6
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354532B2

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