Dichloromethane → Methyl 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate

HRID 518791노트

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HRID 518791 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.[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.CC(N=P(N1CCCC1)(N1CCCC1)N1CCCC1)(C)C.ClCCl>O1CCOCC1.Cl[Pd]Cl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([C:9]2[C:7]3[N:8]=[C:3]([S:2][CH3:1])[N:4]=[CH:5][C:6]=3[S:11][C:10]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:27][CH:26]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 2856454-Fluorophenylboronic acidHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneHCID 86697952HCID 86697952, 화합물

생성물 1

HCID 86697960Methyl 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate수율 78.4%

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

A mixture of 200 mg of methyl 2-(methylsulfanyl)-7-{[(trifluoromethyl)sulfonyl]oxy}thieno[3,2-d]pyrimidine-6-carboxylate 4 (example 1), 216 mg of 4-fluorophenylboronic acid, 19 mg of dichloropalladium (dppf) and 322 mg of BTPP in 2.5 ml of dioxane under argon is microwave-heated at 120° C. in a sealed tube for 1 h. The medium is taken up with dichloromethane and filtered. The organic phase is washed three times with water, then dried over magnesium sulfate, filtered, and then concentrated under vacuum so as to give a yellow solid. The crude is purified on 80 g of silica, elution being carried out with 0-20% of methanol in dichloromethane, so as to obtain 135 mg of methyl 7-(4-fluorophenyl)-2-(methylsulfanyl)thieno[3,2-d]pyrimidine-6-carboxylate in the form of a yellow solid.

후처리

  1. filtrationfiltered
  2. washThe organic phase is washed three times with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum so as
  6. customto give a yellow solid
  7. customThe crude is purified on 80 g of silica, elution

출처 및 근거

ORD 기록
ord-6866c4218d694f1fa1f171f7a538c073
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115140B2

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