Trityl chloride → HCID 11495602、化合物

HRID 908508ノート

反応式

HRID 908508 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 11495602HCID 11495602、化合物収率 86%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b6de8363a8bd44ff85a183aad90f8f4a
出典データセット
uspto-grants-2011_09
特許番号
US08017620B2

反応ノート

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