Trisodium Phosphate → 1-(2-Deoxypentofuranosyl)-5-(hydroxymethyl)-4-imino-1,4-dihydropyrimidin-2-ol

HRID 366969Notes

Reaction equation

HRID 366969 reaction equation
[CH3:1][C:2]1[C:3]([NH2:17])=[N:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1.P([O-])([O-])([O-])=[O:19].[Na+].[Na+].[Na+]>>[OH:19][CH2:1][C:2]1[C:3]([NH2:17])=[N:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:11]([CH2:12][OH:13])[C@@H:9]([OH:10])[CH2:8]1

Participants

3

Reactant 2

HCID 24243Trisodium PhosphateHCID 4400551-(2-Deoxypentofuranosyl)-4-imino-5-methyl-1,4-dihydropyrimidin-2-ol

Product 1

HCID 1690161-(2-Deoxypentofuranosyl)-5-(hydroxymethyl)-4-imino-1,4-dihydropyrimidin-2-ol

Conditions

Temperature
75 °C

Procedure

5-Hydroxymethyldeoxycytidine is synthesized according to the published procedure of Itahara et al. (Chem. Lett. 1591-1594, 1991). To 5-methyl-2'-deoxycytidine (0.5 mmol, available from Sigma Chemical Company) in 100 mL of sodium phosphate buffer (pH 7.0) NasS2O8 (0.5 mmol) is added and the reaction mixture stirred at 75° C. for 4 hours under argon. The reaction mixture is then concentrated and the crude 5-hydroxymethyldeoxycytidine is purified on a LiChroprep reversed-phase HPLC column by eluting with 0.05 M sodium phosphate (pH 7.0) and evaporation of the appropriate fractions.

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. customthe crude 5-hydroxymethyldeoxycytidine is purified on a LiChroprep reversed-phase HPLC column
  3. washby eluting with 0.05 M sodium phosphate (pH 7.0) and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-e40a63065b404b20af2855ba750d44c0
Source dataset
uspto-grants-2000_10
Patent number
US06132776

Reaction notes

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