3-Benzoyl-1-[(E)-4-(trityloxy)-2-butenyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedione → 1-[(E)-4-trityloxy-2-butenyl]uracil

HRID 1713360Notes

Reaction equation

HRID 1713360 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.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 594637583-Benzoyl-1-[(E)-4-(trityloxy)-2-butenyl]-1,2,3,4-tetrahydro-2,4-pyrimidinedioneHCID 178418582HCID 178418582, compound

Product 1

HCID 115680401-[(E)-4-trityloxy-2-butenyl]uracilYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound (12) (50 mg, 0.09 mmol) was dissolved and stirred at room temperature in a solution 0.2 M (5 ml) of MeONa in MeOH. The reaction was left at room temperature overnight, then the solution was neutralized with Dowex H+ ion exchange resin. The resin was filtered off and the filtrate was concentrated under reduced pressure to an oil which was purified by chromatography using CHCl3→CHCl3/MeOH 95:5 as gradient which gave the title compound as a white solid (38 mg, 90%). Rf: 0.51 in CHCl3/MeOH 90:10, M.p. 70-72° C.

Workup

  1. filtrationThe resin was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure to an oil which
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-97b643140e8546eabf2e34ddd5143e4d
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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