Propylamine → 1-(5-O-Acetyl-3-Azido-2,3-Dideoxy-beta-D-erythro-pentofuranosyl)-5-Methyl-4-(Propylamino)-2-(1H)-Pyrimidinone

HRID 973799Notes

Reaction equation

HRID 973799 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:16]=[C:15]([CH3:17])[C:14]([N:18]3[CH:22]=NC=N3)=[N:13][C:12]2=[O:23])[CH2:8][C@@H:7]1[N:24]=[N+:25]=[N-:26])(=[O:3])[CH3:2].[CH2:27](N)[CH2:28]C>CC#N>[C:1]([O:4][CH2:5][C@H:6]1[O:10][C@@H:9]([N:11]2[CH:16]=[C:15]([CH3:17])[C:14]([NH:18][CH2:22][CH2:27][CH3:28])=[N:13][C:12]2=[O:23])[CH2:8][C@@H:7]1[N:24]=[N+:25]=[N-:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 474354[(2s,3s,5r)-3-Azido-5-[5-methyl-2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate

Product 1

HCID 867452161-(5-O-Acetyl-3-Azido-2,3-Dideoxy-beta-D-erythro-pentofuranosyl)-5-Methyl-4-(Propylamino)-2-(1H)-Pyrimidinone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(5-O-Acetyl-3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-(1H)-pyrimidinone (0.5 g, 1.4 mMol) was dissolved in dry CH3CN (50 mL) and treated with n-propylamine (0.6 mL, 7 mMol) at ambient temperature for 48 hours. The reaction was evaporated to an oil and chromatographed on silica gel eluted with 20:1 CHCl3/MeOH (v/v). The appropriate fractions were combined and evaporated to give the title compound as a solid: mp=138°-140° C.; UV(nm): at pH 1 λmax=285,217(ε=14900,12200), λmin=246(ε=2500); at pH 13 λmax=274(ε=12500), λmin=250(ε=9000), λsh=236(ε=10000); H NMR(DMSO-d6) δ7.32(s,1H,H6), 7.24-7.18(m,1H,--NH--), 6.13(t,1H,H1',J=6.44 Hz), 4.45-4.40(m,1 H,H3'), 4.23-4.21(m,2H,--NH--CH2--), 4.00-3.92(m,1H,H4'), 3.26-3.19(m,2H,H5'), 2.33-2.26(m,2H,H2'), 2.05(s,3H,acetyl), 1.85(s,3H,5-CH3), 1.57-1.46(m,2H,--CH2--CH3), 0.88-0.81(t,3H,--CH2--CH3).

Workup

  1. customThe reaction was evaporated to an oil
  2. customchromatographed on silica gel
  3. washeluted with 20:1 CHCl3/MeOH (v/v)
  4. customevaporated

Sources & evidence

ORD record
ord-8d6d792b39cb4084ad4b52421800a8a1
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Reaction notes

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