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Trityl chloride → 1-(3-Hydroxymethyl-4-trityloxybutyl)-1H-pyrimidine-2,4-dione

HRID 1713375
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인쇄 미리보기

반응식

HRID 1713375 반응식
[OH:1][CH2:2][CH:3]([CH2:14][OH:15])[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13].C(N(CC)CC)C.[C:23](Cl)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[OH:1][CH2:2][CH:3]([CH2:14][O:15][C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9](=[O:12])[NH:8][C:7]1=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 2896501-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-uracil

생성물 1

HCID 594637571-(3-Hydroxymethyl-4-trityloxybutyl)-1H-pyrimidine-2,4-dione수율 34%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매
HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

To a solution of compound 35 (45 g, 0.213 mol) in dry DMF (225 mL) was added triethylamine (60 mL, 0.425 mol) and stirred at RT for 15 min. The above reaction mixture was cooled to 0° C., added tritylchloride (59 g, 0.213 mol) followed by addition of catalytic amount of 4-DMAP (app. 20 mg) and allowed to stir at RT for 24 h. The reaction was diluted with water (100 mL), extracted with ethyl acetate (5×200 mL), dried and concentrated under vacuum. The crude was purified by column chromatography over silica gel (6% methanol in chloroform) to give the title compound (33 g, 34%). TLC: Chloroform/Methanol, 9:1, Rf=0.5

후처리

  1. customThe above reaction mixture
  2. temperaturewas cooled to 0° C.
  3. stirringto stir at RT for 24 h
  4. extractionextracted with ethyl acetate (5×200 mL)
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe crude was purified by column chromatography over silica gel (6% methanol in chloroform)

출처 및 근거

ORD 기록
ord-5c8e1ce56a3d40f986d532be54d21edd
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795270B2

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