Hydroquinone → HCID 9861916, compound

HRID 2416418Notes

Reaction equation

HRID 2416418 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([O:15][CH3:16])[CH3:14])[C:4](=[O:17])[CH:3]=1.[CH2:18]=[C:19]1[O:23][C:21](=O)[CH2:20]1.[C:24]1(C=CC(O)=CC=1)O>C1C=CC=CC=1>[CH3:24][N:7]1[C:2]2[NH:1][C:19]([CH3:18])=[CH:20][C:21](=[O:23])[C:3]=2[C:4](=[O:17])[N:5]([CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([O:15][CH3:16])[CH3:14])[C:6]1=[O:8]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 12661Diketene2×HCID 69732887HCID 69732887, compound

Product 1

HCID 9861916HCID 9861916, compoundYield 523.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (R)-6-amino-3-(5-methoxyhexyl)uracil (152 mg, 0.595 mmol), diketene (0.07 ml, 0.89 mmol), hydroquinone (7 mg, 0.06 mmol) and benzene (5 ml) was heated at reflux for 3 hours. Another portion of diketene (0.2 ml) was added and heating at reflux was continued for 18 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was partitioned between water (20 ml) and ethyl acetate (20 ml). The organic layer was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-toluene to provide (R)-1,7-dimethyl-3-(5-methoxyhexyl)pyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (101 mg, 53% yield) as an oil which crystallized on standing. 1H NMR (300 MHz, CDCl3) δ 1.13 (d, 3H), 1.30-1.79 (m, 6H), 2.48 (s, 3H), 3.29 (m, 1H), 3.30 (s, 3H), 3.75 (s, 3H), 4.02 (t, 2H), 6.50 (s, 1H), 12.21 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureheating
  4. temperatureat reflux
  5. concentrationthe mixture was concentrated under reduced pressure
  6. customThe residue was partitioned between water (20 ml) and ethyl acetate (20 ml)
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-toluene

Sources & evidence

ORD record
ord-7fef6de39fef40ad9f9403a055b8f5aa
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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