Hydrochloric Acid → 3-Ethoxy-2-hydroxy-5-(2-oxo-6-phenyl-5-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidin-4-yl)benzonitrile

HRID 924864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924864
[CH2:1]([O:3][C:4]1[C:5]([OH:14])=[C:6]([CH:9]=[C:10]([CH:12]=O)[CH:11]=1)[C:7]#[N:8])[CH3:2].[C:15]1([C:21](=O)[CH2:22][C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH2:29][C:30]([NH2:32])=[O:31].Cl>C(O)C>[CH2:1]([O:3][C:4]1[C:5]([OH:14])=[C:6]([CH:9]=[C:10]([CH:12]2[C:22]([C:23]3[CH:27]=[CH:26][S:25][CH:24]=3)=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:32][C:30](=[O:31])[NH:29]2)[CH:11]=1)[C:7]#[N:8])[CH3:2]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 122331131-Phenyl-2-(thiophen-3-yl)ethanone2×HCID 866693323-Ethoxy-5-formyl-2-hydroxybenzonitrile2×

Produkt 1

HCID 513489503-Ethoxy-2-hydroxy-5-(2-oxo-6-phenyl-5-(thiophen-3-yl)-1,2,3,4-tetrahydropyrimidin-4-yl)benzonitrileAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3-ethoxy-5-formyl-2-hydroxybenzonitrile (Intermediate 51) (70 mg, 0.37 mmol), 1-phenyl-2-(thiophen-3-yl)ethanone (Intermediate 2) (50 mg, 0.28 mmol) and urea (71 mg, 1.1 mmol) in 3 mL of ethanol was added 0.2 mL of concentrated HCl. Refluxed for 2 days. Solvent removed and resulting residue was purified by prep-HPLC (0.1% TFA as additive) to give Compound 105 (18 mg, yield 12%). 1H NMR (DMSO-d6 300 MHz): δ 10.33 (s, 1H), 8.70 (s, 1H), 7.51 (s, 1H), 7.37-7.10 (m, 8H), 6.84 (s, 1H), 6.22 (d, J=4.8 Hz, 1H), 5.16 (d, J=2.4 Hz, 1H), 4.07 (q, J=6.9 Hz, 2H), 1.35 (t, J=6.9 Hz, 3H). MS (ESI): m/z 418.0 [M+1]+.

Aufarbeitung

  1. temperatureRefluxed for 2 days
  2. customSolvent removed
  3. customresulting residue
  4. customwas purified by prep-HPLC (0.1% TFA as additive)

Quellen und Nachweise

ORD-Eintrag
ord-03c377689622461b8cc59f240c21a70b
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09283229B2

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