Sodium Carbonate → HCID 58742226, 화합물

HRID 1514440

반응식

HRID 1514440 반응식
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[S:12][C:13](B2OC(C)(C)C(C)(C)O2)=[C:14]([CH3:16])[N:15]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:11]1[S:12][C:13]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[C:14]([CH3:16])[N:15]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 38589014-Iodo-2-(methylthio)pyrimidine2회HCID 185257002,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole

생성물 1

HCID 58742226HCID 58742226, 화합물수율 76%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

To a solution of 4-iodo-2-methylsulfanyl-pyrimidine (390 mg, 1.56 mmol), 2,4-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiazole (633 mg, 2.65 mmol added portionwise), Na2CO3 (215 mg, 2.02 mmol), triphenylphosphine (42 mg, 0.15 mmol) in nPrOH (25 ml), Pd(OAc)2 (11 mg, 0.047 mmol) was added and the mixture was refluxed for 2 hour. The solvent was evaporated under vacuum, and the crude was dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and evaporated. A second batch of this compound was prepared according to the same protocol starting from 0.39 mmol of 4-iodo-2-methylsulfanyl-pyrimidine. The residues, deriving from the two batches, were purified by flash chromatography with hexane-ethyl acetate to give the title compound (352, 76% yield).

후처리

  1. additionwas added
  2. temperaturethe mixture was refluxed for 2 hour
  3. customThe solvent was evaporated under vacuum
  4. dissolutionthe crude was dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customevaporated
  8. customA second batch of this compound was prepared
  9. customwere purified by flash chromatography with hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-f1720cfc27794da78a3db6a7e7f88397
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222266B2

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