3-Benzoyl-1-(5-trityloxypentyl)-1H-pyrimidine-2,4-dione → 1-(5-Trityloxypentyl)pyrimidine-2,4-dione

HRID 908515Notes

Reaction equation

HRID 908515 reaction equation
C([N:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]1=[O:41])(=O)C1C=CC=CC=1>[OH-].[Na+].O1CCOCC1.[Cl-].[Na+].O>[C:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]1[CH:12]=[CH:13][C:14](=[O:15])[NH:9][C:10]1=[O:41])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 1

HCID 114975923-Benzoyl-1-(5-trityloxypentyl)-1H-pyrimidine-2,4-dione

Product 1

HCID 115973701-(5-Trityloxypentyl)pyrimidine-2,4-dione

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Compound (15) (231 mg; 0.42 mmol) was stirred for 48 hours at room temperature in a mixture of NaOH 1M and Dioxane 1:1 (8 ml). After 48 hours, Brine (8 ml) was added to the solution, and then extracted with EtOAc (3×8 ml). The organic phase was dried over MgSO4; the solvent was removed in vacuo and the crude residue was purified by flash chromatography using DCM/MeOH 90:10 as eluent. The title compound was obtained as a colourless oil which precipitated after treatment with a mixture of Water/EtOH 1:1 which gave the title compound as a white solid (112 mg, 60%). Rf: 0.64 in DCM/MeOH 90:10.

Workup

  1. extractionextracted with EtOAc (3×8 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent was removed in vacuo
  4. customthe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fd08e226a59d4183b3f7d25a8d2fdcaa
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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