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

HRID 963382

반응식

HRID 963382 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-d1816e94275d4658bdec119882c1cb10
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763450

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