Styrene → HCID 53842034, compound

HRID 1178216Notes

Reaction equation

HRID 1178216 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]2[C:4](=[N:5][CH:6]=[C:7](Cl)[N:8]=2)[N:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:41]=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][C:2]1[N:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH:41]=[CH:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[N:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 14971577HCID 14971577, compound

Product 1

HCID 53842034HCID 53842034, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.5 g (5.6 mmoles) 2-amino-6-chloro-4-n-pentyloxypteridine (e.g. available following the procedure disclosed by Mohr et al. in Helv. Chem. Acta (1992) 75:2317), palladium acetate (63 mg, 0.28 mmoles), tri-o-tolylphosphane (682 mg, 2.24 mmoles), cuprous iodide (53 mg, 0.28 mmoles), styrene (1,3 ml., 11.3 mmoles) and triethylamine 3.1 ml, 22 mmoles) was stirred in dry acetonitrile (50 ml) under reflux for 90 hours. It was evaporated and the residue purified by silica gel column chromatography with chloroform. The product fraction was evaporated to give 1.37 g (yield: 72%) of an orange powder exhibiting, after recrystallization from a EtOAc/hexane mixture, a melting point (m.p.) range of 127–128° C.

Workup

  1. temperatureunder reflux for 90 hours
  2. customIt was evaporated
  3. customthe residue purified by silica gel column chromatography with chloroform
  4. customThe product fraction was evaporated

Sources & evidence

ORD record
ord-f4c1e4cd11bd4004a3d3a2cbe8246863
Source dataset
uspto-grants-2007_10
Patent number
US07276506B2

Reaction notes

Loading…