Isopropanol → 2-Chloro-7-phenylthieno[3,2-d]pyrimidine

HRID 1615594노트

반응식

HRID 1615594 반응식
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

참가 물질

7

반응물 4

HCID 3776IsopropanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 569657247-Bromo-2-chlorothieno(3,2-d)pyrimidine

생성물 1

HCID 582288992-Chloro-7-phenylthieno[3,2-d]pyrimidine수율 141.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 7-bromo-2-chlorothieno[3,2-d]pyrimidine (1.0 g, 4.0 mmol), phenyl boronic acid (0.6 g, 4.9 mmol), Pd[PPh3]4 (0.47 g, 0.4 mmol) and aqueous sodium carbonate (2M, 4.5 mL, 9.0 mmol) in toluene (25 mL)/isopropanol (8 mL) was heated under reflux overnight. The mixture was allowed to cool to room temperature, was diluted with ethyl acetate then washed with 10% aqueous sodium bicarbonate, dried (Na2SO4) filtered and concentrated. The resultant solid was sonicated in diethyl ether (2×70 mL) and the combined ether washes were evaporated to afford the crude product (1.4 g), still containing starting material and OPPh3.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. washthen washed with 10% aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was sonicated in diethyl ether (2×70 mL)
  8. customthe combined ether washes were evaporated

출처 및 근거

ORD 기록
ord-1a584c265713426bba2a9c9fac3c58d2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765755B2

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