Hydrochloric Acid → 5-(3,4-Dimethoxy-5-styryl-benzyl)pyrimidine-2,4-diamine

HRID 963390

Reaction equation

HRID 963390 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16](I)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([CH:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]=1[O:18][CH3:19])[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7501StyreneHCID 8471TriethylamineHCID 111010945-(3,4-Dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine

Product 1

HCID 542175855-(3,4-Dimethoxy-5-styryl-benzyl)pyrimidine-2,4-diamineYield 53.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 500 mg of 5-(3,4-dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamine, 1.53 g of styrene, 1.46 g of triethylamine and 31 mg of palladium-(II) acetate in 25 ml of dioxan is held at reflux under argon for 14 hrs. The mixture is poured on to ice-water, adjusted to pH 5 to 7 with 3N aqueous hydrochloric acid and extracted with methylene chloride. The organic phase is dried over magnesium sulphate, concentrated and the residue is chromatographed on silica gel with methylene chloride/methanol 97:3. 252 mg (53%) of 5-(3,4-dimethoxy-5-styryl-benzyl)pyrimidine-2,4-diamine are isolated as an orange solid. M.p.226°.

Workup

  1. temperatureat reflux under argon for 14 hrs
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated
  5. customthe residue is chromatographed on silica gel with methylene chloride/methanol 97:3

Sources & evidence

ORD record
ord-3f97be4ee11d4e57b9cc1dd1d49000af
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Linked notes

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