Ethyl Acetate → Methyl 6-(bromomethyl)-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

HRID 131575Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 131575
OC1CON(C([C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH:21]([CH3:23])[CH3:22])[C:12]=3[S:11][C:10]=2CC2C3C(=NC=CC=3)NC=2)=O)C1.[Br:34]N1C(=O)CCC1=O.[C:42]([O:45][CH2:46]C)(=[O:44])[CH3:43]>>[Br:34][CH2:9][C:10]1[S:11][C:12]2[N:13]([CH:21]([CH3:23])[CH3:22])[C:14](=[O:20])[N:15]([CH3:19])[C:16](=[O:18])[C:17]=2[C:43]=1[C:42]([O:45][CH3:46])=[O:44]

Komponenten

4

Edukt 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 688045155-[[4-Hydroxyisoxazolidin-2-yl]carbonyl]-3-methyl-1-(1-methylethyl)-6-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 68806593Methyl 6-(bromomethyl)-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate

Versuchsvorschrift

A solution of the product of example 8, part b), (1.6 g), N-bromosuccinimide (1 g), and azoisobutyronitrile (10 mg) in ethyl acetate (25 ml) was refluxed for 1 h. The solution was cooled to room temperature, washed successively with dilute sodium hydroxide solution and water, the organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with diethyl ether/i-hexane (1:1) to give the sub-title compound as a solid (1.5 g). δ 1HCDCl3 1.62 (6H, d), 3.37 (3H, s), 3.99 (3H, s), 3.60-3.70 (3H, m)

Aufarbeitung

  1. washwashed successively with dilute sodium hydroxide solution and water
  2. dry with materialthe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography over silica
  6. washeluting with diethyl ether/i-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-994d91ccabf24a9196d60c7d5ed6ddd0
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384950B2

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