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

HRID 908529Notes

Reaction equation

HRID 908529 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-75d5b72615494185a9fc19bf77a10d0d
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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