Water → HCID 11750725, compound

HRID 908510Notes

Reaction equation

HRID 908510 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8].[C:14]1([C:20](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>N1C=CC=CC=1>[C:20]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:13]=[CH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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 3

HCID 962WaterHCID 6456Trityl chlorideHCID 4535651-((2-Hydroxyethoxy)methyl)uracil

Product 1

HCID 11750725HCID 11750725, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(2-hydroxy-ethoxymethyl)uracil (0.50 g, 2.69 mmol) and triphenylmethyl chloride (0.82 g, 2.96 mmol) were stirred in dry pyridine (20 ml) overnight at 50° C. under an atmosphere of nitrogen. H2O (10 ml) was added and the mixture was extracted with CHCl3 (2×50 ml), dried (Na2SO4) and reduced in vacuo to obtain a crude product, which was purified by column chromatography eluting with 0→3% MeOH/CHCl3 to obtain the title compound as a white solid (0.23 g, 20%).

Workup

  1. extractionthe mixture was extracted with CHCl3 (2×50 ml)
  2. dry with materialdried (Na2SO4)
  3. customto obtain a crude product, which
  4. customwas purified by column chromatography
  5. washeluting with 0→3% MeOH/CHCl3

Sources & evidence

ORD record
ord-471822a03cc8444c8e356b93ad3dfa7c
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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