(Z)-1-Ethoxy-2-(tributylstannyl)ethene → HCID 69014896, compound

HRID 2099251Notes

Reaction equation

HRID 2099251 reaction equation
[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[N:14]=[C:13](Br)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([O:28][CH:29]=[CH:30][Sn](CCCC)(CCCC)CCCC)[CH3:27]>CN(C=O)C>[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[N:14]=[C:13]([CH:27]=[CH:26][O:28][CH2:29][CH3:30])[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 24851847HCID 24851847, compound

Product 1

HCID 69014896HCID 69014896, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1,9-dibenzyl-6,9-dihydro-6-oxo-8-bromopurine (20) (1.20 g, 3.04 mmol) bis(triphenylphosphine)palladium(II)chloride (0.213 g, 0.3 mmol) and ethoxyvinyl-(tributyl)tin (2.19 g, 6.07 mmol) in dry DMF (50 mL) was heated under N2 at 70° C. for 22 h. DMF was distilled off and the resulting residue dissolved in EtOAc (100 ml) and filtered through a pad of celite. The solvent was distilled off and the residue was purified by flash chromatography (EtOAc:hexane, 6:4). Yield 0.989 g (88%). Mp 167-168° C. 1H NMR (CDCl3) δ 1.26 (t, 3H, CH3, J=7.5 Hz), 3.86 (q, 2H, CH2J=7 Hz), 4.46 (d, 1H, CH, J=2.5 Hz), 5.26 (s, 2H, benzylic CH2), 5.32 (d, 1H, CH2 J=3 Hz), 5.60 (s, 2H, benzylic C2), 7.10-7.37 (m, 10H, Ar—H) 7.99 (s, 1H, purine C2—H). 13C NMR (CDCl3) δ 14.1, 47.8, 49.1, 63.8, 90.2, 123.5, 126.6, 126.6, 127.5, 127.5, 128.2, 128.7, 128.7, 128.9, 129.1, 129.1, 136.2, 136.7, 146.2, 146.9, 148.9, 151.9, and 156.6. FAB-HRMS: [M+H]+ Calcd. for C23H23N4O2 387.1821. Found 387.1815.

Workup

  1. distillationDMF was distilled off
  2. dissolutionthe resulting residue dissolved in EtOAc (100 ml)
  3. filtrationfiltered through a pad of celite
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by flash chromatography (EtOAc:hexane, 6:4)

Sources & evidence

ORD record
ord-c11906e7e0004ac685e7e7c1d1f214f6
Source dataset
uspto-grants-2009_08
Patent number
US07569573B2

Reaction notes

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