Methylhydrazine → HCID 19993538, compound

HRID 345069Notes

Reaction equation

HRID 345069 reaction equation
[Si:1]([O:8][CH:9]([CH2:32][O:33][CH2:34][P:35]([O:40][CH2:41][CH3:42])([O:37][CH2:38][CH3:39])=[O:36])[CH2:10][O:11][N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[N:21]1C(=O)C2=CC=CC=C2C1=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CNN>ClCCl>[Si:1]([O:8][CH:9]([CH2:32][O:33][CH2:34][P:35]([O:40][CH2:41][CH3:42])([O:37][CH2:38][CH3:39])=[O:36])[CH2:10][O:11][N:12]1[CH:20]=[N:19][C:18]2[C:13]1=[N:14][CH:15]=[N:16][C:17]=2[NH2:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 19993504HCID 19993504, compound

Product 1

HCID 19993538HCID 19993538, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 9-[2-(t-butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy)propoxy]-6-phthalimidopurine (0.99 g, 1.6 mmol) in dichloromethane (10 ml) was cooled to 0° C., treated with methylhydrazine (0.lml, 1.76 mmol) and stirred at 20° C. for 1.5 h. The reaction mixture was filtered and evaporated in vacuo and the residue dissolved in ether. The ether was filtered, evaporated in vacuo and the residue chromatographed twice on silica, eluting firstly with chloroform-methanol 20:1 and then with chloroform, to give 9-[2-(t -butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy)propoxy]adenine (480mg, 61%) as a clear oil. νmax (film) 3350, 1650, 1600 and 1590 cm-1 ; δH (CDCl3) 0.07 (6H, S, CH3SiCH3), 0.88 (9H, S, (CH3)3CSi), 1.34 (6H, t, J6.8 Hz, 2×CH3CH2), 3.75 (2H, d, J5.2 Hz, CH2OCH2P), 3.87 (2H, d, J8.2 Hz, CH2P), 4.17 (4H, m, 2×CH3CH2), 4.22 (1H, m, CHOSi), 4.42 (1H, m, CH2ON), 4.53 (1H, m, CH2ON), 5.71 (2H, br.s, D2O exchangeable, NH2), 7.99 (1H, s, H-2/H-8), 8.36 (1H, s, H-2/H-8). Found: C, 45.57; H, 7.40; N, I3.65%; [M-H]+ 488.0297. C19H36N5O6PSi.0.7H2O requires C, 45.44; H, 7.50; N, 13.94%; [M-H]+ 488.0294.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated in vacuo
  3. dissolutionthe residue dissolved in ether
  4. filtrationThe ether was filtered
  5. customevaporated in vacuo
  6. customthe residue chromatographed twice on silica
  7. washeluting firstly with chloroform-methanol 20:1

Sources & evidence

ORD record
ord-0f4ce18185ef424cbfc79638b891c1de
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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