Triphenylphosphine → 2-Chloro-4-(5-chloro-2-thienyl)thieno[3,2-d]pyrimidine

HRID 131192

반응식

HRID 131192 반응식
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20][C:21]1[N:22]=[C:23](Cl)[C:24]2[S:29][CH:28]=[CH:27][C:25]=2[N:26]=1.[Cl:31][C:32]1[S:36][C:35](B(O)O)=[CH:34][CH:33]=1.C([O-])(O)=O.[Na+]>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:20][C:21]1[N:22]=[C:23]([C:35]2[S:36][C:32]([Cl:31])=[CH:33][CH:34]=2)[C:24]2[S:29][CH:28]=[CH:27][C:25]=2[N:26]=1

참가 물질

8

반응물 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 27343245-Chlorothiophene-2-boronic acidHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

생성물 1

HCID 865923142-Chloro-4-(5-chloro-2-thienyl)thieno[3,2-d]pyrimidine수율 94%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of Pd(OAc)2 (12 mg, 5 mol %) and PPh3 (52 mg, 20 mol %) in THF (2 mL) was stirred for 5 min, treated dropwise with a solution of 2,4-dichlorothieno[3,2-d]pyrimidine (205 mg, 1 mmol) in THF (1 mL), stirred for 5 min, treated with 5-chlorothiophene-2-boronic acid (244 mg, 1.5 mmol) then saturated aqueous NaHCO3 (1 mL) refluxed for 4 h, cooled, diluted with H2O and filtered to give the title compound (268 mg, 94%) as a grey solid; NMR δH (400 MHz, CDCl3) 7.10 (1H, d, J 4.0 Hz), 7.55 (1H, d, J 5.5 Hz), 7.85 (1H, d, J 4.5 Hz) and 8.08 (1H, d, J 5.5 Hz)

후처리

  1. temperaturecooled
  2. filtrationfiltered

출처 및 근거

ORD 기록
ord-b0560a529aba4ddaa1d8f109dcf0e96e
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384949B2

연결된 노트

불러오는 중…