Triphenylphosphine → HCID 11754512, compound

HRID 1708098

Reaction equation

HRID 1708098 reaction equation
[OH:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].O[CH2:23][CH2:24]/[CH:25]=[CH:26]\[P:27](=[O:34])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:32]([O:31][P:27](/[CH:26]=[CH:25]\[CH2:24][CH2:23][O:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([O:28][CH2:29][CH3:30])=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10081772HCID 10081772, compoundHCID 145239709-Hydroxy-6-phthalimidopurine

Product 1

HCID 11754512HCID 11754512, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 9-hydroxy-6-phthalimidopurine (320 mg, 1.14 mmol) , diethyl (Z)-4-hydroxybut-1-enylphosphonate (250 mg, 1.20 mmol) and triphenyl phosphine (448 mg, 1.71 mmol) in dry tetrahydrofuran (11 ml) stirred at 0° C. under dry nitrogen was added diethyl azodicarboxylate (296 mg, 170 mmol). The mixture was allowed to warm to r.t. and stirred for 2.3 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with acetone-hexane (1:1, 4:3) to give (Z)-9-[4-(diethoxyphosphoryl)but-3-enyloxy]-6-phthalimidopurine as a light brown gum (320 mg, 60%); λmax (EtOH) 271 (14,680)nm; υmax (KBr) 2980, 1735, 1595, 1575, 1360, 1330, 1245 and 1025 cm-1 ; δH [(CD3)2SO] 1.23 (6H, t, J 7 Hz, CH3), 3.05 (2H, m, CH2), 3.98 (4H, dq, J 7 Hz and 8Hz, CH2CH 3), 4.63 (2H, t, J 6 Hz, CH2O ), 5.90 (1H, dd, J 14 Hz and 20 Hz, PCH=CH), 6.75 (1H, ddt, J 7 Hz, 14 Hz and 52 Hz, PCH=CH), 8.05 (4H, m, C6H4), 9.05 (1H, s, H-2/H-8), 9.10 (1H, s, H-2/H-8) (Found: C, 53.77; H, 4.87; N, 14.52%; MH+ 472.1384. C21H22N5O6P requires C, 53.50; H, 4.70; N, 14.86%; MH+ 472.1386).

Workup

  1. temperatureto warm to r.t.
  2. stirringstirred for 2.3 hr
  3. customThe solvent was removed
  4. customthe residue was purified by column chromatography on silica gel eluting with acetone-hexane (1:1, 4:3)

Sources & evidence

ORD record
ord-2f7678df38634b6ab8fcf1b788e1e8a0
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Linked notes

Loading…