Methanol → 6-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid

HRID 131556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131556
[OH-].[Na+].CO.[Cl:5][C:6]1[N:7]=[C:8]([CH3:33])[N:9]([CH2:12][C:13]2[S:28][C:16]3[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[C:15]=3[C:14]=2[C:29]([O:31]C)=[O:30])[C:10]=1[Cl:11]>O1CCCC1>[Cl:5][C:6]1[N:7]=[C:8]([CH3:33])[N:9]([CH2:12][C:13]2[S:28][C:16]3[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[C:15]=3[C:14]=2[C:29]([OH:31])=[O:30])[C:10]=1[Cl:11]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 11453923Methyl 6-[4,5-dichloro-2-methyl-1H-imidazol-1-ylmethyl]-1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-thieno[2,3-d]pyrimidine-5-carboxylate

Produkt 1

HCID 113628036-[(4,5-Dichloro-2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,4-tetrahydro-3-methyl-1-(isobutyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydroxide (7.3 ml of 1M aqueous solution) followed by methanol (4 ml) were added to a solution of the product of step c) (2.28 g) in tetrahydrofuran (50 ml) and stirred at room temperature for 3 h. The solution was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica chromatography eluting with a gradient of 2-5% ethanol in dichloromethane to give the sub-title compound as a white solid (1.68 g). MS (APCI) 445/447 [M+H]+. δ 1HCDCl3 0.96 (6H,d), 2.22 (1H, septet), 2.37 (3H,s), 3.51 (3H,s), 3.78 (2H,d), 5.78 (2H,s), 15.51 (1H,br.s).

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash silica chromatography
  8. washeluting with a gradient of 2-5% ethanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-263ec2d36204410a833f7f2d11602e2e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384950B2

Notizen zur Reaktion

Wird geladen…