Acetic Acid → 6-Amino-9-(2-chloroethyl)-2-[(3-pyridylmethyl)amino]-purine

HRID 1920665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1920665
[Cl:1][CH2:2][CH2:3][N:4]1[CH:12]=[N:11][C:10]2[C:5]1=[N:6][C:7]([NH2:14])=[N:8][C:9]=2[NH2:13].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=O)[CH:16]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[NH2:13][C:9]1[N:8]=[C:7]([NH:14][CH2:21][C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[N:6]=[C:5]2[C:10]=1[N:11]=[CH:12][N:4]2[CH2:3][CH2:2][Cl:1]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 103713-Pyridinecarboxaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 668680839-(2-Chloroethyl)-2,6-diamino-purine

Produkt 1

HCID 668680516-Amino-9-(2-chloroethyl)-2-[(3-pyridylmethyl)amino]-purineAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

100 mg (0.47 mmol) of 9-(2-chloroethyl)-2,6-diamino-purine (example 12, step A) were dissolved in 10 ml MeOH and 3 g molecular sieves (4 Å), 0.044 ml (0.47 mmol) 3-pyridinecarboxaldehyde and 0.135 ml (2.35 mmol) acetic acid were added. The mixture was stirred for 2 hours at room temperature. 23.6 mg (0.38 mmol) sodium cyano-borohydride were added and stiffing was continued for 4 hours. Additional 0.044 ml (0.47 mmol) 3-pyridinecarboxaldehyde were added and 72 mg sodium cyano-borohydride were added in three portions over three days at room temperature. The solvent was evaporated and the residue was taken up in 50 ml ethyl acetate. The organic layer was washed with sat. aqueous sodium carbonate and brine, dried over Na2SO4 and the solvent was evaporated in vacuo to give 0.254 g of the crude product as yellow oil. The crude product was purified by flash chromatography on silica gel (DCM/MeOH 99.5/0.5→80:20) to give 88 mg of the desired product as white solid.

Aufarbeitung

  1. waitstiffing was continued for 4 hours
  2. customThe solvent was evaporated
  3. washThe organic layer was washed with sat. aqueous sodium carbonate and brine
  4. dry with materialdried over Na2SO4
  5. customthe solvent was evaporated in vacuo
  6. customto give 0.254 g of the crude product as yellow oil
  7. customThe crude product was purified by flash chromatography on silica gel (DCM/MeOH 99.5/0.5→80:20)

Quellen und Nachweise

ORD-Eintrag
ord-7d7ee3473dee47f2a9164dbd8035c2ce
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173609B2

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