Hydrochloric Acid → 3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehyde

HRID 426176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426176
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([C:11]([C:13]2[C:18]([CH:19]([CH3:21])[CH3:20])=[C:17]([O:22][CH3:23])[N:16]=[C:15]([O:24][CH3:25])[N:14]=2)=[O:12])[CH:7]=[C:8]([CH3:10])[CH:9]=1.Cl>C(Cl)(Cl)Cl.CO>[CH:19]([C:18]1[C:13]([C:11]([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([CH3:10])[CH:7]=2)[CH:3]=[O:2])=[O:12])=[N:14][C:15]([O:24][CH3:25])=[N:16][C:17]=1[O:22][CH3:23])([CH3:21])[CH3:20]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 59184803(3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

Produkt 1

HCID 591848613-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehydeAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of (3-dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone (3.13 g, 8.36 mmol) in chloroform (30 ml) at room temperature, was added hydrogen chloride in methanol solution [prepared from methanol (30 ml) and acetyl chloride (4 ml)]. After stirring for 2 hr., the mixture was evaporated in vacuo. The residue was dissolved in ether, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, i) MC, ii) MC:EA (9:1)) to afford 2.3 g (84%) of a white solid. m.p. 111-113° C.; 1H NMR (300 MHz, CDCl3) δ 1.20 (6H, d, J=7.2 Hz), 2.50 (3H, s), 2.85 (1H, m), 3.93 (3H, s), 4.08 (3H, s), 7.94 (1H, s), 7.99 (1H, s), 8.08 (1H, s), 10.02 (1H, s).

Aufarbeitung

  1. custom, the mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with aqueous saturated sodium bicarbonate solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, i) MC, ii) MC

Quellen und Nachweise

ORD-Eintrag
ord-4a73cc4c04c0445d875efba507738d51
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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