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

HRID 973800Notes

Reaction equation

HRID 973800 reaction equation
C([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][CH2:19][CH2:20][CH3:21])=[N:13][C:12]2=[O:22])[CH2:8][C@@H:7]1[N:23]=[N+:24]=[N-:25])(=O)C>N>[N:23]([C@@H:7]1[C@@H:6]([CH2:5][OH:4])[O:10][C@@H:9]([N:11]2[CH:16]=[C:15]([CH3:17])[C:14]([NH:18][CH2:19][CH2:20][CH3:21])=[N:13][C:12]2=[O:22])[CH2:8]1)=[N+:24]=[N-:25]

Participants

3

Reactant 1

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

Product 1

HCID 867452171-(3-Azido-2,3-Dideoxy-beta-D-erythro-pentofuranosyl)-5-Methyl-4-(Propylamino)-2-(1H)-Pyrimidinone

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

1-(5-O-Acetyl-3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-methyl-4-(propylamino)-2-(1H)-pyrimidinone (0.3 g, 0.8 mMol,EX.) was dissolved in NH3 saturated MeOH (15 mL). After 3 hours the solvents were evaporated in vacuo to yield the title compound as a solid: mp=59°-62° C.; UV(nm): at pH 1 λmax=288,219(ε=11300,9500), λmin=247(ε=1700); at pH 13 λmax=276(ε=9000), λmin=253(ε=6400); H NMR(DMSO-d6) δ7.54(s,1H,H6), 7.17(t,1H,--NH--), 6.08(t,1H,H1',J=6.45 Hz), 5.17(t,1H,5'OH), 4.33(q,1H,H3'), 3.79(q,1H,H4'), 3.65-3.55(m,2H,--NH--CH2--), 3.26-3.19(m,2H,H5'), 2.22(t,2H,H2'), 1.83(s, 3H,5-CH3), 1.6-1.4(m,2H,--CH2--CH3), 0.84(t,3H,--CH2--CH3).

Workup

  1. customAfter 3 hours the solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-ee80471679134ae78f5243702197b53c
Source dataset
uspto-grants-1991_11
Patent number
US05064946

Reaction notes

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