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

HRID 131575ノート

反応式

HRID 131575 の反応式
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]

参加物

4

反応物 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

生成物 1

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

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-994d91ccabf24a9196d60c7d5ed6ddd0
出典データセット
uspto-grants-2008_06
特許番号
US07384950B2

反応ノート

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