Triphenylphosphine → 3-benzoyl-1-[(Z)-4-(trityloxy)-2-butenyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione

HRID 1713354Notes

Reaction equation

HRID 1713354 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([N:28]1[C:33](=[O:34])[CH:32]=[CH:31][NH:30][C:29]1=[O:35])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:36]([O:55][CH2:56][CH:57]=[CH:58][CH2:59]O)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CCCCCC.CCOC(C)=O>[C:20]([N:28]1[C:33](=[O:34])[CH:32]=[CH:31][N:30]([CH2:59]/[CH:58]=[CH:57]\[CH2:56][O:55][C:36]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:29]1=[O:35])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5695133-BenzoyluracilHCID 5363146Diisopropyl azodicarboxylateHCID 541104114-Trityloxy-but-2-en-1-ol

Product 1

HCID 594637643-benzoyl-1-[(Z)-4-(trityloxy)-2-butenyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedioneYield 29%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Polymer bound triphenylphosphine (0.75 g; 2.25 mmol) was shaken in THF (5 ml) for 15 minutes, then 3-benzoyluracil (290 mg, 1.35 mmol) and tritylated alcohol (1) (300 mg; 0.90 mmol) were added to the suspension of the resin. A solution of DIAD (0.354 ml, 1.80 mmol) in THF (2 ml) was added to the mixture. The reaction was shaken 24 hours at room temperature and monitored by TLC (Hexane/EtOAc 50:50). The resin was filtered and washed twice with THF (5 ml). The filtrate was concentrated under reduced pressure and taken in EtOAc (5 ml), a white solid precipitated. The precipitate was filtered, the filtrate was concentrated again and purified by flash chromatography using Hexane/EtOAc as eluent which gave the title compound as a colourless oil (136 mg, 29%).

Workup

  1. filtrationThe resin was filtered
  2. washwashed twice with THF (5 ml)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customa white solid precipitated
  5. filtrationThe precipitate was filtered
  6. concentrationthe filtrate was concentrated again
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-fdd44ff610564336b7dd61acbe8bef8f
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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