Triphenylphosphine → HCID 87973076, compound

HRID 1072970Notes

Reaction equation

HRID 1072970 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[CH2:5][C:6]1[N:11]([CH2:12][O:13][CH2:14]CO)[C:10](=[O:17])[NH:9][C:8](=[O:18])[C:7]=1[CH2:19][CH3:20].O([C:32]([NH:34][O:35]C(OC1C=CC=CC=1)=O)=O)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=[N:71]/[C:72]([O:74]C(C)C)=O)=O)C>O1CCCC1.CCOCC>[OH:35][N:34]([CH2:32][CH2:14][O:13][CH2:12][N:11]1[C:6]([CH2:5][C:4]2[CH:3]=[C:2]([CH3:1])[CH:23]=[C:22]([CH3:24])[CH:21]=2)=[C:7]([CH2:19][CH3:20])[C:8](=[O:18])[NH:9][C:10]1=[O:17])[C:72]([NH2:71])=[O:74]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 4531502,4(1H,3H)-Pyrimidinedione, 6-((3,5-dimethylphenyl)methyl)-5-ethyl-1-((2-hydroxyethoxy)methyl)-HCID 5363146Diisopropyl azodicarboxylateHCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamine

Product 1

HCID 87973076HCID 87973076, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 6-(3,5-dimethylbenzyl)-5-ethyl-1-(2-hydroxyethoxymethyl)uracil (0.2 g, 0.6 mmol), N,O-bis(phenoxycarbonyl)hydroxylamine (0.18 g, 0.66 mmol) and triphenylphosphine (0.19 g, 0.66 mmol) in tetrahydrofuran (6 ml) was added dropwise at 0° C. DIAD (diisopropylazodicarboxylate) (145 mg, 0.71 mmol). The reaction medium, concentrated, was subjected successively to two flash column chromatographies on silica gel, the first one using a mixture dichloromethane/methanol 49:1 as eluant and the second one, the mixture ethyl acetate/petroleum ether 2:3. It was thus obtained 6-(2,3-dimethyl-benzyl)-5-ethyl-1-(2-N,O-bis(phenoxycarbonyl)hydroxyaminoethoxymethyl) uracil (0.30 g, 85%), 0.15 g (0.25 mmol) which was dissolved in a ammonia saturated methanolic solution (10 ml) and stirred for 24 h at 10° C. The reaction medium, concentrated, subjected to a flash column chromatography on silica gel (dichloromethane/methanol 19:1) gave an oil which, taken again with ether, gave the 1-(2-N1-hydroxyureidoethoxymethyl)-6-(3,5-dimethylbenzyl)-5-ethyl-uracil (36.6 mg, 36%) in the form of a white solid.

Workup

  1. customThe reaction medium
  2. concentrationconcentrated
  3. dissolutionwas dissolved in a ammonia saturated methanolic solution (10 ml)
  4. customThe reaction medium
  5. concentrationconcentrated
  6. customgave an oil which

Sources & evidence

ORD record
ord-55be5c70e7d54535b8da1a71b9c69cd8
Source dataset
uspto-grants-2005_06
Patent number
US06911450B1

Reaction notes

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