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Piperidine → HCID 178422580, Verbindung

HRID 635706
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 635706
C[C:2]1OC(C)=[CH:5][C:6]=1[N:7]1CC[CH2:9][CH2:8]1.[C:13]([C:16]1[CH:20]=[C:19]([CH3:21])[O:18][C:17]=1[CH3:22])(=O)[CH3:14].N1CCCC1.[CH3:28][C:29]1[N:34]=[C:33](Cl)[C:32]([N+:36]([O-])=O)=[C:31](Cl)[N:30]=1.C(N(CC)C(C)C)(C)C.N1CCCCC1.Cl[Sn]Cl.[OH-].[Na+]>CN(C=O)C.Cl[Ti](Cl)(Cl)Cl.CCN(CC)CC>[CH3:22][C:17]1[O:18][C:19]([CH3:21])=[CH:20][C:16]=1[C:13]1[CH:14]=[C:31]2[NH:30][C:29]([CH:28]3[CH2:9][CH2:8][NH:7][CH:6]([CH3:5])[CH2:2]3)=[N:34][CH:33]=[C:32]2[N:36]=1
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Komponenten

12

Edukt 8

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 31268PyrrolidineHCID 615273-Acetyl-2,5-dimethylfuranHCID 81531DiisopropylethylamineHCID 831924,6-Dichloro-2-methyl-5-nitropyrimidine
HCID 12413714
2,5-Dimethyl-3-[1-pyrrolidinyl]furan

Produkt 1

HCID 178422580HCID 178422580, VerbindungAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24193Titanium TetrachlorideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Using the method described in Example 30 by employing 2,5-dimethyl-3-[1-pyrrolidinyl]furan (freshly prepared before use from 3-acetyl-2,5-dimethylfuran (Aldrich Chemical Company), pyrrolidine and TiCl4 (4.88 g, 25.5 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (5.30 g, 25.5 mmol), N,N-diisopropyl ethylamine (4.5 mL, 25.5 mmol), piperidine (4.0 mL, 40.8 mmol), NEt3 (4.0 mL) and SnCl2 (77 mL of a 2 M soln in DMF). Note because of the increase in scale, the workup involved NaOH (15 g) and crushed ice (300 mL). The residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant to give 1.01 g (13%) of 2,5-dimethyl-3-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)furan as a beige colored powder. This material (1.01 g, 3.22 mmol) was dissolved in 2:1 EtOAc/MeOH (100 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (3.25 mL, 3.25 mmol). The solution was left to cool to room temperature. The resulting crystals were collected by filtration, washed with EtOAc (2×10 mL), Et2O (3×15 mL) and dried under vacuum at 60° C. to give 878 mg (10%) of the title compound as a white colored solid. Mp: 238-240° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.69 (br s, 6), 2.29 (s, 3), 2.44 (s, 3), 2.55 (s, 3), 4.01 (s, 4), 6.47 (s, 1), 6.55 (s, 1), 11.67 (s, 1), 14.18 (s, 1). MS m/z: 311 (M+1 for free base). Anal. Calcd for C18H22N4O.HCl.1.0H2O: C, 59.25; H, 6.91; N, 15.36; Cl, 9.72. Found: C, 59.19; H, 6.80; N, 15.30; Cl, 9.88.

Aufarbeitung

  1. temperatureincrease in scale
  2. customThe residue was purified by flash chromatography on silica gel with 95:5 CHCl3/MeOH as eluant

Quellen und Nachweise

ORD-Eintrag
ord-a1531bc5dd7242b0b2af1bfb58dc8f49
Quelldatensatz
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06187777B1

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