Benzaldehyde → 2-Amino-5-benzylaminomethylpyrrolo[2,3-d]pyrimidin-4-one

HRID 1903313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903313
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH2:12])=[C:5]2[C:4](=[O:13])[N:3]=1.C[O-].[Na+].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+].Cl.N.C(O)C>CO>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]=[CH:9][C:10]([CH2:11][NH:12][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:5]2[C:4](=[O:13])[N:3]=1

Komponenten

8

Edukt 6

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 202463772-Amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-oneHCID 22020343Ethanol, reaction products with ammonia, distn. residues

Produkt 1

HCID 204685402-Amino-5-benzylaminomethylpyrrolo[2,3-d]pyrimidin-4-oneAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 5 ml of methanol was dissolved 251 mg of 2-amino-5-aminomethylpyrrolo[2,3-d]pyrimidin-4-one (dihydrochloride). To this solution was added 396 mg of a 28% methanolic solution of sodium methoxide, and under stirring at room temperature, 106 mg of benzaldehyde and, then, 1 g of molecular sieve (Wako Pure Chemical Co. in Japan 3 A 1/16) were added. The mixture was stirred for 30 minutes, after which 25 mg of sodium borohydride was added. The mixture was further stirred at room temperature for 30 min., and 0.3 ml of concentrated HCl and, then, 5 ml of 5.4% ammonia-ethanol were added. The insolubles were filtered off, the filtrate was concentrated, and the residue was purified by silica gel column chromatography to give 214 mg of the desired compound.

Aufarbeitung

  1. additionin Japan 3 A 1/16) were added
  2. stirringThe mixture was stirred for 30 minutes
  3. stirringThe mixture was further stirred at room temperature for 30 min.
  4. filtrationThe insolubles were filtered off
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2b2f596435e54021afc60b0c45b85fea
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04435569

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