Dichloromethane methanol → 1-(4-Trityloxy-but-2-enyl)-1H-pyrimidine-2,4-dione

HRID 1713355Notes

Reaction equation

HRID 1713355 reaction equation
C([N:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16]/[CH:17]=[CH:18]\[CH2:19][O:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]1=[O:40])(=O)C1C=CC=CC=1.C(Cl)Cl.CO>CO[Na].CO>[C:21]([O:20][CH2:19][CH:18]=[CH:17][CH2:16][N:11]1[CH:12]=[CH:13][C:14](=[O:15])[NH:9][C:10]1=[O:40])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 21226129Dichloromethane methanolHCID 594637643-benzoyl-1-[(Z)-4-(trityloxy)-2-butenyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

Product 1

HCID 668412961-(4-Trityloxy-but-2-enyl)-1H-pyrimidine-2,4-dioneYield 94.2%

Reagents, catalysts & solvents 1

HCID 178501943HCID 178501943, compoundSolvent

Procedure

A suspension of compound (2) (50 mg; 0.095 mmol) in MeONa/MeOH 0.2 M (5 ml) was stirred at room temperature for 24 hours. During such period of time the suspension became a colourless solution and the TLC (DCM/MeOH 90:10) showed the complete disappearance of the starting amide, and the presence of a new spot at lower Rf. The solution was neutralised with Dowex ion exchange resin. The resin was filtered off and washed twice with MeOH (5 ml). The filtrate was concentrated under reduced pressure and purified by flash chromatography using MeOH/DCM 10:90 as eluent which gave the title compound as a white solid (38 mg, 90%). Rf: 0.66 in DCM/MeOH 90:10.

Workup

  1. waitDuring such period of time the suspension became
  2. filtrationThe resin was filtered off
  3. washwashed twice with MeOH (5 ml)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2712d17e21234d52aa4eccb8be917225
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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