(1H-indol-5-yl)methanamine → 2-Amino-6-(2-furyl)-N-(5-indolylmethyl)pyrimidine-4-carboxamide

HRID 254158

Reaktionsgleichung

Reaktionsgleichung von HRID 254158
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1.[NH:16]1[C:24]2[C:19](=[CH:20][C:21]([CH2:25][NH2:26])=[CH:22][CH:23]=2)[CH:18]=[CH:17]1.N=C=N.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:26][CH2:25][C:21]2[CH:20]=[C:19]3[C:24](=[CH:23][CH:22]=2)[NH:16][CH:17]=[CH:18]3)=[O:10])[CH:5]=[C:4]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Komponenten

6

Edukt 4

HCID 54791(1H-indol-5-yl)methanamineHCID 160435CarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 287995992-Amino-6-(2-furyl)pyrimidine-4-carboxylic acid

Produkt 1

HCID 113595262-Amino-6-(2-furyl)-N-(5-indolylmethyl)pyrimidine-4-carboxamideAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture consisting of 2-amino-6-(2-furyl)pyrimidine-4-carboxylic acid (206 mg, 1.0 mmol), indole-5-methanamine (146 mg, 1.0 mmol), polymer supported carbodiimide (Argonaut Technologies, loading 1.38 mmol/g, 1.10 g, 1.5 mmol) and 1-hydroxybenzotriazole hydrate (203 mg, 1.5 mmol) in DMF (5 mL) was stirred at room temperature for 24 hr. The mixture was filtered through a pad of Celite, washing through with EtOAc. The filtrate was washed successively with H2O (10 mL), 2-M Na2CO3 (2×10 mL) and H2O (10 mL), dried (MgSO4) and concentrated in vacuo. The resulting oil was dissolved in MeOH (1.0 mL), added dropwise with stirring to H2O (2 mL) and the resulting precipitate filtered to give the title compound (198 mg, 59%) as a cream solid.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing through with EtOAc
  3. washThe filtrate was washed successively with H2O (10 mL), 2-M Na2CO3 (2×10 mL) and H2O (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting oil was dissolved in MeOH (1.0 mL)
  7. additionadded dropwise
  8. stirringwith stirring to H2O (2 mL)
  9. filtrationthe resulting precipitate filtered

Quellen und Nachweise

ORD-Eintrag
ord-9cc58eadd0584f6a90a024859fd625e1
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875600B2

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