Methylhydrazine → 9-[2-(Diethoxyphosphorylmethylthio)-ethoxy]adenine

HRID 1031071Notes

Reaction equation

HRID 1031071 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][S:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[N:23]1C(=O)C2=CC=CC=C2C1=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].CNN>>[CH2:1]([O:3][P:4]([CH2:9][S:10][CH2:11][CH2:12][O:13][N:14]1[CH:22]=[N:21][C:20]2[C:15]1=[N:16][CH:17]=[N:18][C:19]=2[NH2:23])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 198195589-[2-(Diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine

Product 1

HCID 198195779-[2-(Diethoxyphosphorylmethylthio)-ethoxy]adenineYield 75%

Procedure

A solution of 9-[2-(diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine (0.56 g, 1.lmmol) was cooled to 0°-5° C. and treated with N-methylhydrazine (0.86 g, 1.8 mmol). The mixture was stirred for 1 hour, and then filtered and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel, using dichloromethane: methanol (97:3) as eluent, to give the title compound (0.3 g, 75%) as colourless crystals after b crystallisation from acetone, m.p. 93°-95° C.; γmax (MeOH) 260nm (ε 12670); υmax (KBr) 3360, 3280, 3140, 2995, 1685, 1610, 1570, 1480, 1410, 1370, 1330, 1300, and 1260cm-1 ; 6H [(CD3)2SO]1.25 (6H. t, J 8Hz 2 × CH3), 3.0 (2H, d, J 13Hz PCH2S), 3.1 (2H, t, J 7Hz, CH2O), 4.1 (4H, m, 2 × CH2), 4.6 (2H, t, J 7Hz, CH2S), 7.4 (2H, br.s, exchangeable with D2O, NH2), 8.15 (1H, s, 2-H), 8.4 (1H, s, 8-H) (Found: C, 39.84; H, 5.51; N, 19.26%; M+ 361.0981. C12H2O N5O4PS requires C, 39.88; H, 5.58; N, 19.38%; M+ 361.0974).

Workup

  1. filtrationfiltered
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4f1d203d5b344697a10e442cedb7d528
Source dataset
uspto-grants-1992_04
Patent number
US05108994

Reaction notes

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