Potassium Carbonate → 5-(4'-Dimethylamino-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine

HRID 963382

反応式

HRID 963382 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.[CH3:21][N:22]([CH3:33])[C:23]1[CH:28]=[CH:27][C:26](OB(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[CH3:21][N:22]([CH3:33])[C:23]1[CH:28]=[CH:27][C:26]([C:16]2[C:17]([O:18][CH3:19])=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([CH2:6][C:7]3[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=3)[CH:15]=2)=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 111010945-(3,4-Dimethoxy-5-iodo-benzyl)pyrimidine-2,4-diamineHCID 190817074-Dimethylamino-phenylboric acid

生成物 1

HCID 190816835-(4'-Dimethylamino-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine収率 91%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

376 mg of 5-(3,4-dimethoxy-5-iodo-benzyl)-pyrimidine-2,4-diamine and 400 mg of 4-dimethylamino-phenylboric acid (Example 3a)) are treated with 40 ml of dioxan and 2.4 ml of a 2M potassium carbonate solution and 24 mg of tetrakis-tri-phenylphosphine-palladium. The mixture is heated at reflux under argon for 14 hrs. Subsequently, it is poured on to ice-water, extracted with methylene chloride, dried over magnesium sulphate and chromatographed on silica gel with methylenechloride/methanol 98:2. 327 mg (91%) of 5-(4'-dimethylamino-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a yellowish solid. M.p. 230°.

後処理

  1. temperatureThe mixture is heated
  2. temperatureat reflux under argon for 14 hrs
  3. extractionextracted with methylene chloride
  4. dry with materialdried over magnesium sulphate
  5. customchromatographed on silica gel with methylenechloride/methanol 98:2

出典と根拠

ORDレコード
ord-d1816e94275d4658bdec119882c1cb10
出典データセット
uspto-grants-1998_06
特許番号
US05763450

関連ノート

読み込み中…