Trityl chloride → HCID 11495602, compound

HRID 908508Notes

Reaction equation

HRID 908508 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 11495602HCID 11495602, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b6de8363a8bd44ff85a183aad90f8f4a
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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