Pivaloyl chloride → 1-(3-Azido-2,3-dideoxy-5-O-pivaloyl-beta-D-erythro-pentofuranosyl)-5-methyl-2(1H)-pyrimidinone

HRID 2248854Notes

Reaction equation

HRID 2248854 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:12]2=[O:18])[CH2:5]1)=[N+:2]=[N-:3].[C:19](Cl)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>N1C=CC=CC=1>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[O:7][C@@H:6]([N:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:12]2=[O:18])[CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 62493Pivaloyl chlorideHCID 4515791-(3-Azido-2,3-dideoxy-beta-D-erythropentofuranosyl)-5-methyl-2(1H)-pyrimidinone

Product 1

HCID 867449971-(3-Azido-2,3-dideoxy-5-O-pivaloyl-beta-D-erythro-pentofuranosyl)-5-methyl-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(3-Azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-2(1H)-pyrimidinone (0.4 g, 1.59 mMol) was dissolved in dry pyridine (10 mL) at 0° C. under a nitrogen atmosphere. Pivaloyl chloride (0.588 mL; 4.78 mMol) was added with stirring and allowed to react for 72 hours. The reaction was quenched with ice then evaporated to dryness. The residue was chromatographed on silica gel eluted with 20:1 CHCl3 /MeOH (v/v) and the appropriate fractions combined and evaporated to give the title compound: mp =121°-123° C.; UV (nm): at pH 1λmax =327 (ε=5900), λmin =269 (ε=820); at pH 13λmax =322 (ε=17200), λmin =251 (ε=850); 1H NMR: (DMSO-d6) δ8.48(d, J=3.12 Hz, 1H, H4), 7.88(d, J=3.27 Hz, 1H, H6), 6.02(t, J=6.25 Hz, 1H, H1 '), 4.48-4.39(m, 1H, H3 '), 4.31-4.28(m, 2H, H5 '), 4.20-4.14(m, 1H, H4 '), 2.62-2.50(m, 1H, H2 '), 2.41-2.27(m, 1H, H2 '), 2.04(s, 3H, 5-CH3), 1.12(s, 9H, -C(CH3)3).

Workup

  1. customto react for 72 hours
  2. customThe reaction was quenched with ice
  3. customthen evaporated to dryness
  4. customThe residue was chromatographed on silica gel
  5. washeluted with 20:1 CHCl3 /MeOH (v/v)
  6. customevaporated

Sources & evidence

ORD record
ord-d9144e31699b4cc1a5c567cd8c67724f
Source dataset
uspto-grants-1991_08
Patent number
US05041543

Reaction notes

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