Triphenylphosphine → HCID 19993545, compound

HRID 345071

Reaction equation

HRID 345071 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([OH:23])[CH2:11][CH2:12][O:13][CH2:14][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][CH:28]=[N:29][C:30]=2[N:34]1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Si:1]([O:8][CH2:9][CH:10]([O:23][N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][CH:28]=[N:29][C:30]=2[N:34]1[C:35](=[O:44])[C:36]2=[CH:43][CH:42]=[CH:41][CH:40]=[C:37]2[C:38]1=[O:39])[CH2:11][CH2:12][O:13][CH2:14][P:15]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 145239709-Hydroxy-6-phthalimidopurineHCID 19993524HCID 19993524, compound

Product 1

HCID 19993545HCID 19993545, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of diethyl 4-t-butyldimethylsilyloxy-3-hydroxybutoxymethylphosphonate (0.49 g, 1.31 mmol), 9-hydroxy-6-phthalimidopurine (0.5 g, 1.31 mmol) and triphenylphosphine (0.52 g, l.97 mmol) in dry tetrahydrofuran (50 ml) was stirred under nitrogen at O° C. during the addition of diethyl azodicarboxylate (0.31 ml, 1.97 mmol). The solution was then stirred at 20° C. for 4 h and evaporated in vacuo. The residue was chromatographed on silica, eluting with hexane-acetone 4:1, affording 9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-phthalimidopurine (575mg, 69%) as a clear oil. νmax (film) 3500, 1790, 1740, 1600 and 1580 cm-1 ; δH [(CD3)2SO] 0.04 (6H, s, CH3SiCH3), 0.74 (9H, s, (CH3)3CSi), 1.22 (6H, t, J6.9 Hz, 2×CH3CH 2), 2.04 (2H, m, SiOCH2CHCH2), 3.79 (2H, m, CH2OSi), 3.88 (2H, d, J8.2 Hz, CH2P), 3.96 (2H, m, CH2OCH2P), 4.03 (4H, m, 2×CH3CH2), 4.69 (1H, m, CHON), 8.05 (4H, m, ArH), 8.91 (1H, s, H-2/H-8), 9.07 (1H, s, H-2/H-8); m/z (FAB+ve Ion), 656 (MNa+) and 634 (MH+). Found: C, 53.10 H, 6.30; N, 10.83%; C28H40N5O8PSi requires C, 53.07; H, 6.36,; N, 11.05%.

Workup

  1. customevaporated in vacuo
  2. customThe residue was chromatographed on silica
  3. washeluting with hexane-acetone 4:1

Sources & evidence

ORD record
ord-d0b43dfccfdf4ca88bd8794b186fd02f
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Linked notes

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