Phosgene → 6-(2-Furyl)-9-(1-pyrrolidinylcarbonyl)-9H-purine-2-amine

HRID 271259

Reaktionsgleichung

Reaktionsgleichung von HRID 271259
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6](Cl)(Cl)=[O:7].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[NH:23][C:22]([NH2:24])=[N:21][C:20]2[C:16]=1[N:17]=[CH:18][N:19]=2.CCN(CC)CC>C1(C)C=CC=CC=1.O>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[N:23]=[C:22]([NH2:24])[N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[C:6]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7]

Komponenten

7

Edukt 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

Produkt 1

HCID 598349776-(2-Furyl)-9-(1-pyrrolidinylcarbonyl)-9H-purine-2-amineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of pyrrolidine (50 mL, 0.6 mmol) in toluene (2 mL) was treated with a solution of phosgene in toluene (0.31 mL, 1.93-M, 0.6 mmol), heated at 80° C. for 30 mins, cooled and concentrated in vacuo. The residue was dissolved in THF (2 mL) and added to a solution of 6-(2-furyl)-1H-purine-2-amine (100 mg, 0.5 mmol) and Et3N (83 mL, 0.6 mmol) in DMP (0.5 mL), stirred at 60° C. for 16 h, poured into water and extracted with EtOAc. The combined organic phase was dried (MgSO4), concentrated in vacuo and the resulting solid triturated with EtOAc/heptane and filtered to give the title compound (92 mg, 62%) as a cream solid.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in THF (2 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe resulting solid triturated with EtOAc/heptane
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-aa7f95a0fb27463884a087d55b99382d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452894B2

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