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

HRID 963390

반응식

HRID 963390 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.[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-3f97be4ee11d4e57b9cc1dd1d49000af
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763450

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