Hydroquinone → HCID 69733596, compound

HRID 2416433Notes

Reaction equation

HRID 2416433 reaction equation
[C:1]([O:4][C@H:5]([CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH:14]=[C:13]([NH2:17])[N:12]([CH3:18])[C:11]1=[O:19])(=[O:3])[CH3:2].[CH2:21]=[C:22]1O[C:24](=[O:25])[CH2:23]1.C1(C=CC(O)=CC=1)O>ClC(Cl)C>[C:1]([O:4][C@H:5]([CH3:20])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[C:14]2[C:24](=[O:25])[CH:23]=[C:22]([CH3:21])[NH:17][C:13]=2[N:12]([CH3:18])[C:11]1=[O:19])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 12661DiketeneHCID 54017983HCID 54017983, compound

Product 1

HCID 69733596HCID 69733596, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of (R)-3-(5-acetoxyhexyl)-6-amino-1-methyluracil (3.0 g, 10.6 mmol), diketene (1.2 ml, 15.9 mmol), hydroquinone (50 mg, 0.45 mmol) and dichloroethane (100 ml) was heated at reflux for 36 hours. After cooling to room temperature, the solution was washed with water, dried over sodium sulfate, and concentrated under vacuum. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-toluene followed by 50% ethyl acetate-toluene) to provide (R)-3-(5-acetoxyhexyl)-1,7-dimethylpyrido[2,3-d]pyrimidine-2,4,5(1H,3H,8H)-trione (1.45 g, 39% yield) followed by (R)-3-(5-acetoxyhexyl)-1,5-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (1.26 g, 34% yield). 1H NMR (300 MHz, CDCl3) δ 1.17 (d, 3H), 1.28-1.67 (m, 6H), 1.99 (s, 3H), 2.67 (s, 3H), 3.59 (s, 3H), 3.95 (t, 2H), 4.85 (sextet, 1H), 6.23 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 19.65, 21.16, 22.58, 22.74, 27.31, 29.87, 35.25, 41.34, 70.88,100.16, 109.56, 150.05, 150.49, 156.07,160.41, 164.03,171.07.

Workup

  1. temperatureat reflux for 36 hours
  2. washthe solution was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate-toluene

Sources & evidence

ORD record
ord-87a61517c82048b2ae887c344f572831
Source dataset
uspto-grants-2004_11
Patent number
US06825180B2

Reaction notes

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