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

HRID 131575노트

반응식

HRID 131575 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

실험 절차

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)

후처리

  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)

출처 및 근거

ORD 기록
ord-994d91ccabf24a9196d60c7d5ed6ddd0
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384950B2

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