Water → Methyl 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

HRID 131555Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131555
[Cl:1][C:2]1[N:3]=[C:4]([CH3:8])[NH:5][C:6]=1[Cl:7].[H-].[Na+].Br[CH2:12][C:13]1[S:28][C:16]2[N:17]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:18](=[O:23])[N:19]([CH3:22])[C:20](=[O:21])[C:15]=2[C:14]=1[C:29]([O:31][CH3:32])=[O:30].O>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([CH3:8])[N:5]([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][CH3:32])=[O:30])[C:6]=1[Cl:7]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3123904,5-Dichloro-2-methyl-1H-imidazoleHCID 16102871Methyl 6-bromomethyl-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Produkt 1

HCID 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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

4,5-Dichloro-2-methylimidazole (1.3 g) in dry tetrahydrofuran (20 ml) was added dropwise to a suspension of sodium hydride (0.34 g, 60%) in dry tetrahydrofuran (20 ml) at room temperature under nitrogen. After 15 min, a solution of the product of step b) (3.35 g) in dry tetrahydrofuran (20 ml) was added dropwise and the reaction was stirred for 3 h at room temperature. The solution was poured into 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 50-100% ethyl acetate in isohexane to give the sub-title compound as a white solid (2.28 g). MS (APCI) 459/460 [M+H]+. δ 1HCDCl3 0.97 (6H,d), 2.26 (1H, septet), 2.38(3H,s), 3.39 (3H,s), 3.73 (2H,d), 3.99 (3H,s), 5.26 (2H,s).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash silica chromatography
  6. washeluting with a gradient 50-100% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-c0deaf4660514eaaa2f69860ba8ba17d
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384950B2

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