Triethyl Phosphate → HCID 15160070, compound

HRID 1089315Notes

Reaction equation

HRID 1089315 reaction equation
[C@@H:1]1([N:10]2[CH:15]=[C:14]3[CH:16]=[CH:17][C:18](=[O:20])[N:19]=[C:13]3[NH:12][C:11]2=[O:21])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].P(Cl)(Cl)(Cl)=O.[CH2:27](OP(OCC)(OCC)=O)C>>[C@@H:1]1([N:10]2[CH:15]=[C:14]3[CH:16]=[CH:17][C:18](=[O:20])[N:19]([CH3:27])[C:13]3=[N:12][C:11]2=[O:21])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

4

Reactant 3

HCID 6535Triethyl PhosphateHCID 24813Phosphorus oxychlorideHCID 178515721HCID 178515721, compound

Product 1

HCID 15160070HCID 15160070, compound

Procedure

A solution of 560 mg of 3-β-D deoxyribofuranosyl-2,7-dioxopyrido[2,3-d]pyrimidine (a) in 5 ml of triethylphosphate was cooled to 0° C. and 613 mg of phosphorus oxychloride was added thereto. After the mixture was made to undergo a reaction for 6 hours, 1 g of ice was added to effect a hydrolysis. The reaction mixture was concentrated at reduced pressure and the resulting residue was dissolved in 1 ml of distilled water. The purification of the product was carried out by column chromatography on DEAE-Sephadex A-25 (HCO3 -form) by use of a linear gradient of triethylammonium bicarbonate to obtain 575 mg of 3-(5'-O-phosphoryl-β-D-2'-deoxyribofuranosyl)-2,7-dioxopyrido[2,3-d]pyrimidine (b).

Workup

  1. customa reaction for 6 hours
  2. customa hydrolysis
  3. concentrationThe reaction mixture was concentrated at reduced pressure
  4. dissolutionthe resulting residue was dissolved in 1 ml of distilled water
  5. customThe purification of the product

Sources & evidence

ORD record
ord-ebabc65a3fda43849c5b92324e00def6
Source dataset
uspto-grants-1990_10
Patent number
US04965350

Reaction notes

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