N-(4-Bromobutyl)phthalimide → 4-Amino-2-(4-phthalimidobutylthio)pyrimidine

HRID 34778

Reaktionsgleichung

Reaktionsgleichung von HRID 34778
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[S:3].N12CCCCC1C=NCCC2.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>C(O)C>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]=[C:2]([S:3][CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[C:29](=[O:30])[C:28]3=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]3[C:26]2=[O:35])[N:4]=1

Komponenten

5

Edukt 3

HCID 93575N-(4-Bromobutyl)phthalimideHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 178507915HCID 178507915, Verbindung

Produkt 1

HCID 212987544-Amino-2-(4-phthalimidobutylthio)pyrimidineAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2-thiocytosine (0.25 g.), 1,5-diazabicyclo[5,4,0]undec-5-ene (0.33 g.), ethanol (10 ml.) and N-(4-bromobutyl)phthalimide (0.62 g.) was stirred at room temperature for 18 hours and then evaporated to dryness. The residue was partitioned between water and ethyl acetate and the ethyl acetate phase was dried and evaporated to dryness. The residue was recrystallised from acetonitrile to give 4-amino-2-(4-phthalimidobutylthio)pyrimidine (0.56 g.), m.p. 164°-167°.

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialthe ethyl acetate phase was dried
  4. customevaporated to dryness
  5. customThe residue was recrystallised from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a682a20e344347838a09dbb729f50832
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762932

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