Phenylboronic Acid → Methyl 2-(methylthio)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate

HRID 518783노트

반응식

HRID 518783 반응식
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9](OS(C(F)(F)F)(=O)=O)[C:7]=2[N:8]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C>Cl[Pd]Cl.O1CCOCC1>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[S:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:7]=2[N:8]=1

참가 물질

6

반응물 3

HCID 66827Phenylboronic AcidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86697952HCID 86697952, 화합물

생성물 1

HCID 86697951Methyl 2-(methylthio)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate수율 78.6%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 312751,4-Dioxane용매

실험 절차

Anhydrous dioxane is added, under argon, to a mixture of 2.5 g of methyl 2-(methylsulfanyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 4 (example 1) and 0.785 g of phenylboronic acid. After the addition of 250 mg of dichloropalladium (dppf) and 4.09 g of BTPP, the mixture is refluxed for 20 h, and then cooled to ambient temperature. The mixture is filtered on silica gel, elution being carried out with ethyl acetate. The solvent is evaporated off under vacuum and the residue is triturated with an ethyl acetate/heptane mixture so as to obtain 1.6 g of methyl 2-(methylsulfanyl)-7-phenylthieno[3,2-d]pyrimidine-6-carboxylate in the form of a whitish precipitate.

후처리

  1. temperaturethe mixture is refluxed for 20 h
  2. filtrationThe mixture is filtered on silica gel, elution
  3. customThe solvent is evaporated off under vacuum
  4. customthe residue is triturated with an ethyl acetate/heptane mixture so as

출처 및 근거

ORD 기록
ord-1ab7a8cf87c04e34a5341b129eba1404
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115140B2

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