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Diisopropylethylamine → 2-{4-[5-(2-Diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol

HRID 2069428
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2069428
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[N:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[C:6]([CH3:13])[N:5]=1)[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.O[NH:48][C:49](=[NH:59])[C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57][OH:58])=[CH:52][CH:51]=1>CN(C=O)C.CCOC(C)=O.O1CCOCC1>[CH2:14]([N:3]([CH2:1][CH3:2])[C:4]1[N:9]=[C:8]([C:10]2[O:12][N:59]=[C:49]([C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH2:57][OH:58])=[CH:52][CH:51]=3)[N:48]=2)[CH:7]=[C:6]([CH3:13])[N:5]=1)[CH3:15]
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Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 242773182-(Diethylamino)-6-methylpyrimidine-4-carboxylic acidHCID 59604233CID 59604233

Produkt 1

HCID 685054582-{4-[5-(2-Diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanolAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-diethylamino-6-methylpyrimidine-4-carboxylic acid (1.31 g, 6.28 mmol) in DMF (20 mL) is added DIPEA (3.23 mL, 18.8 mmol) followed by TBTU (2.62 g, 8.17 mmol). The mixture is stirred at rt for 10 min before N-hydroxy-4-(2-hydroxy-ethyl)-benzamidine (1.24 g, 6.91 mmol) is added. After stirring for 1 h, the reaction mixture is diluted with EtOAc and the solution is washed with sat. aq. NaHCO3. The aq. phase is extracted with EtOAc and the combined org. extracts are dried over MgSO4, filtered and concentrated to give the crude hydroxyamidine ester intermediate (3.56 g). This material is dissolved in dioxane (50 mL) and the resulting solution is stirred at 85° C. for 16 h. The solvent is evaporated and the crude product is purified by CC (eluting with EtOAc/Heptane 1:4) to give 2-{4-[5-(2-diethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenyl}-ethanol as a yellow solid (1.30 g); LC-MS: tR=1.07 min; [M+H]+=354.07. 1H NMR (CDCl3): δ 1.25 (t, J=7.0 Hz, 6H), 1.45 (m, 1H), 2.47 (s, 3H), 2.98 (t, J=6.5 Hz, 2H), 3.75 (q, J=7.0 Hz, 4H), 3.95 (m, 2H), 7.23 (s, 1H), 7.41 (d, J=7.8 Hz, 2H), 8.15 (d, J=7.5 Hz, 2H).

Aufarbeitung

  1. additionis added
  2. washthe solution is washed with sat. aq. NaHCO3
  3. extractionThe aq. phase is extracted with EtOAc
  4. dry with materialextracts are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude hydroxyamidine ester intermediate (3.56 g)
  8. stirringthe resulting solution is stirred at 85° C. for 16 h
  9. customThe solvent is evaporated
  10. customthe crude product is purified by CC (eluting with EtOAc/Heptane 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-719c55a66cdd4d2aae8c69664107398c
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299086B2

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