Sodium Hydroxide → 4-benzyloxy-3-ethyl-N-[2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide

HRID 2069471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2069471
[CH2:1]([O:8][C:9]1[C:36]([CH3:37])=[CH:35][C:12]([C:13]([NH:15][CH2:16][C:17](OCC)([O:29]CC)[C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][CH:26]([CH3:28])[CH3:27])[N:19]=2)=[O:14])=[CH:11][C:10]=1[CH2:38][CH3:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.Cl>[CH2:1]([O:8][C:9]1[C:36]([CH3:37])=[CH:35][C:12]([C:13]([NH:15][CH2:16][C:17]([C:18]2[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([NH:25][CH:26]([CH3:28])[CH3:27])[N:19]=2)=[O:29])=[O:14])=[CH:11][C:10]=1[CH2:38][CH3:39])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 685084724-benzyloxy-N-[2,2-diethoxy-2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide

Produkt 1

HCID 685107654-benzyloxy-3-ethyl-N-[2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-2-oxo-ethyl]-5-methyl-benzamideAusbeute 108,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of 4-benzyloxy-N-[2,2-diethoxy-2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-ethyl]-3-ethyl-5-methyl-benzamide (346 mg, 0.65 mmol) in THF (8 mL), 25% aq. HCl (500 μL) is added and the mixture is stirred at 65° C. for 18 h. The mixture is cooled to 0° C., neutralized by adding 1 N aq. NaOH solution and extracted twice with EtOAc. The combined org. extracts are dried over Na2SO4, filtered and concentrated to give crude 4-benzyloxy-3-ethyl-N-[2-(2-isopropylamino-6-methyl-pyrimidin-4-yl)-2-oxo-ethyl]-5-methyl-benzamide (325 mg) as a yellow oil; LC-MS: tR=0.94 min, [M+H]+=461.13.

Aufarbeitung

  1. temperatureThe mixture is cooled to 0° C.
  2. extractionextracted twice with EtOAc
  3. dry with materialextracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6b7a53e05a184e0089b41e5aad390bfa
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299086B2

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