Methylhydrazine → 9-[1-(t-Butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]adenine

HRID 345072

Reaction equation

HRID 345072 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([O:23][N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][CH:27]=[N:28][C:29]=2[N:33]1C(=O)C2=CC=CC=C2C1=O)[CH2:11][CH2:12][O:13][CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CNN>ClCCl>[Si:1]([O:8][CH2:9][CH:10]([O:23][N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][CH:27]=[N:28][C:29]=2[NH2:33])[CH2:11][CH2:12][O:13][CH2:14][P:15]([O:17][CH2:18][CH3:19])([O:20][CH2:21][CH3:22])=[O:16])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 199935459-[1-(t-Butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-phthalimidopurine

Product 1

HCID 199935469-[1-(t-Butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]adenineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-phthalimidopurine (550 mg, 0.87 mmol) in dichloromethane (10 ml) was treated with methylhydrazine (0.05 ml, 0.96 mmol) and stirred for 30 min at 20° C. The reaction mixture was filtered, the solvent evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 40:1, affording 9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)-but-2-oxy]adenine (380mg, 87%) as a clear oil. νmax (film) 3340, 3200, 1730, 1650, 1600 and 1470 cm-1, δH (CDCl3) 0.04 (6H, s, CH3SiCH3), 0.87 (9H, s, (CH3)3CSi), 1.33 (6H, t, J7.1 Hz, 2×CH3CH2), 2.08 (2H, m, SiOCH2CHCH2), 3.80-3.90 (4H, m, CH2OSi+CH2P), 3.99 (2H, m, CH2OCH2P), 4.16 (4H, m, 2×CH3CH2), 4.61 (1H, m, CHON), 5.68 (2H, br.s, D2O exchangeable, NH2), 8.04 (1H, s, H- 2/H-8), 8.34 (1H, s, H-2/H-8); m/z (FAB+ve Ion), 526 (MNa+), 504 (MH+); Found: C, 47.35; H, 7.68; N, 13.67% C20H38N5O6PSi requires C, 47.50; H, 7.60; N, 13.91%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated in vacuo
  3. customthe residue chromatographed on silica
  4. washeluting with chloroform-methanol 40:1

Sources & evidence

ORD record
ord-ecb41c363c374ee6b48280f041d50190
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Linked notes

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