Water → Pyrido[2,3-d]pyrimidine

HRID 1793298Notes

Reaction equation

HRID 1793298 reaction equation
N[C:2]1[C:3]2[C:11](=O)[CH:10]=[CH:9][N:8]([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)[C:4]=2[N:5]=[CH:6][N:7]=1.Cl[Si](C(C)C)(C(C)C)O[Si](Cl)(C(C)C)C(C)C.O>N1C=CC=CC=1>[N:5]1[C:4]2[N:8]=[CH:9][CH:10]=[CH:11][C:3]=2[CH:2]=[N:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1724041,3-DichlorotetraisopropyldisiloxaneHCID 9926133HCID 9926133, compound

Product 1

HCID 582898Pyrido[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A reaction mixture of 4-amino-5-oxo-8-(β-D-ribofuranosyl)pyrido[2,3-d]pyrimidine (1.8 g, 6.20 mmol) and 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (2.15 mL, 6.73 mmol) in anhydrous pyridine (25 mL) was stirred at room temperature for 20 h and cooled with ice. Water (0.5 mL) was added, and the mixture stirred at ambient temperature for 30 min and concentrated. The residue was dissolved in ethyl acetate, washed with diluted sodium bicarbonate, dried over Na2SO4, and concentrated. Chromatography on silica (EtOAc-hexanes 3:2) gave 2.0 g of 4-amino-5-oxo-8-[3,5-O-(1,1,3,3-tetraisopropyldisiloxy)-β-D-ribofuranosyl)]pyrido[2,3-d]pyrimidine.

Workup

  1. temperaturecooled with ice
  2. stirringthe mixture stirred at ambient temperature for 30 min
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with diluted sodium bicarbonate
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-379b0ec7c95d4c418e88f52f69f88941
Source dataset
uspto-grants-2006_07
Patent number
US07081449B2

Reaction notes

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