Chloride → 2-Acetoxyethoxymethyl-6-(3,5-dimethylbenzyl)-5-ethyluracil

HRID 1072969

반응식

HRID 1072969 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[CH2:5][C:6]1[NH:11][C:10](=[O:12])[NH:9][C:8](=[O:13])[C:7]=1[CH2:14][CH3:15].[C:20]([O:23][CH2:24][CH2:25][O:26][CH2:27]OC(=O)C)(=[O:22])[CH3:21].C[Si](C)(C)N[Si](C)(C)C.C[Si](Cl)(C)C.[Cl-].[Na]>C(#N)C.ClCCl>[C:20]([O:23][CH2:24][CH2:25][O:26][CH2:27][N:9]1[C:8](=[O:13])[C:7]([CH2:14][CH3:15])=[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([CH3:1])[CH:18]=[C:17]([CH3:19])[CH:16]=2)[NH:11][C:10]1=[O:12])(=[O:22])[CH3:21]

참가 물질

9

반응물 6

HCID 312ChlorideHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 1009992-((Acetyloxy)methoxy)ethyl acetateHCID 5360545SodiumHCID 106826455-Ethyl-6-(3,5-dimethylbenzyl)uracil

생성물 1

HCID 867597672-Acetoxyethoxymethyl-6-(3,5-dimethylbenzyl)-5-ethyluracil수율 92%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 6344Dichloromethane용매

실험 절차

6-(3,5-dimethylbenzyl)-5-ethyluracil (see the above Example 4-A) (516 mg, 2 mmol) and 1-acetoxy-2-acetoxymethoxyethane [A. Rosowski, S. H. Kim. M. Wick, J. Med. Chem. (1981) 24, 1177-81]) (704 mg, 4 mmol) were suspended, under nitrogen atmosphere, in acetonitrile (20 ml). It was added thereto HMDS (hexamethyldisilazane) (646 mg, 4 mmol) and TMSCl (chlorotrimethyl-silane) (435 mg, 4 mmol) and the mixture was then stirred for 10 mn. Then it was added dropwise thereto, over 10 mn, a solution of tinIV chloride (625 mg, 2.4 mmol) in acetonitrile (5 ml). After 14 h under stirring, it was added thereto dichloromethane (50 ml) and an aqueous saturated sodium hydrogenocarbonate solution (50 ml). The mixture was extracted with dichloromethane (3×50 ml). The organic phases, collected, were washed with a aqueous saturated sodium hydrogenocarbonate solution (25 ml), with water (25 ml), and then with an aqueous saturated sodium chloride solution. The organic phase was dried (sodium sulfate), concentrated, and then subjected to a flash column chromatography (petroleum ether/ethyl acetate 3:2) to give 1-(2-acetoxyethoxymethyl-6-(3,5-dimethylbenzyl)-5-ethyluracil (690 mg, 92%) in the form of a white solid.

후처리

  1. additionIt was added
  2. additionThen it was added dropwise
  3. additionit was added
  4. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  5. customThe organic phases, collected
  6. washwere washed with a aqueous saturated sodium hydrogenocarbonate solution (25 ml), with water (25 ml)
  7. dry with materialThe organic phase was dried (sodium sulfate)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6939d380907641fab71908148bd86667
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911450B1

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