Trityl chloride → HCID 11495602, 화합물

HRID 908508노트

반응식

HRID 908508 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8].[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:14]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

5

반응물 2

HCID 6456Trityl chlorideHCID 123533871-(4-Hydroxybutyl)pyrimidine-2,4(1H,3H)-dione

생성물 1

HCID 11495602HCID 11495602, 화합물수율 86%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

1-(4′-Hydroxybutyl)uracil (0.083 g, 0.45 mmol), trityl chloride (0.140 g, 0.50 mmol) and DMAP (5 mg, 0.05 mmol) were stirred in dry pyridine (6 mL) at 50° C. under nitrogen for 64 h. The reaction mixture was left to cool to room temperature and then partitioned between cold water (20 mL) and DCM (15 mL, 2×10 mL). The organic extracts were combined, washed with brine (20 mL), dried over MgSO4 and concentrated in vacuo. Further purification by silica gel column chromatography (Isolute SI column) using a gradient elution of 0→3% CH3OH in CHCl3. The fractions with Rf=0.58 (10% CH3OH/CHCl3) yielded the title compound as a white solid (0.165 g, 86%).

후처리

  1. waitThe reaction mixture was left
  2. custompartitioned between cold water (20 mL) and DCM (15 mL, 2×10 mL)
  3. washwashed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customFurther purification by silica gel column chromatography (Isolute SI column)
  7. washa gradient elution of 0→3% CH3OH in CHCl3

출처 및 근거

ORD 기록
ord-b6de8363a8bd44ff85a183aad90f8f4a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017620B2

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