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

HRID 963390

反応式

HRID 963390 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-3f97be4ee11d4e57b9cc1dd1d49000af
出典データセット
uspto-grants-1998_06
特許番号
US05763450

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