Dimethylbarbituric acid → HCID 86729324, compound

HRID 1474622Notes

Reaction equation

HRID 1474622 reaction equation
[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:34]=[CH:33][C:32]([O:35]CC=C)=[CH:31][CH:30]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH2:7][O:8]2)(=[O:3])[CH3:2].CN1C(=O)CC(=O)N(C)C1=O>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:4][C@H:5]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@:9]2([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([CH2:28][C:29]4[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=4)[CH:22]=3)[O:20][C@@:6]1([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH2:7][O:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 86729325HCID 86729325, compound

Product 1

HCID 86729324HCID 86729324, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate (0.6 g, 0.973 mmol) in dry THF (10 mL), was added Pd(PPh3)4 (337 mg, 0.29 mmol) followed by 1,3-dimethyl barbituric acid (1.57 g, 9.73 mmol). The reaction mixture was then refluxed at 90° C. for 1 h. After the completion of reaction as monitored by TLC, the reaction was quenched with saturated solution of NaHCO3 (10 mL), diluted with ethyl acetate (100 mL) and then washed with water (3×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 5:5 Ethyl acetate:Pet. Ether) to provide title compound (0.53 g, 94%).

Workup

  1. customAfter the completion of reaction
  2. customthe reaction was quenched with saturated solution of NaHCO3 (10 mL)
  3. additiondiluted with ethyl acetate (100 mL)
  4. washwashed with water (3×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4 and volatiles
  6. customwere evaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (silica gel, 5:5 Ethyl acetate:Pet. Ether)

Sources & evidence

ORD record
ord-7994ba2b262f4b59a8d00fe3388039c0
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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