Potassium Phosphate, Tribasic → 7-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5(6H)-one

HRID 1852988노트

반응식

HRID 1852988 반응식
Cl[C:2]1[NH:7][C:6](=[O:8])[N:5]2[CH:9]=[CH:10][N:11]=[C:4]2[CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[N:22][N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCOCC>[CH3:30][Si:29]([CH3:32])([CH3:31])[CH2:28][CH2:27][O:26][CH2:25][N:23]1[CH:24]=[C:20]([C:2]2[NH:7][C:6](=[O:8])[N:5]3[CH:9]=[CH:10][N:11]=[C:4]3[CH:3]=2)[CH:21]=[N:22]1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 213201027-Chloroimidazo[1,2-c]pyrimidin-5-olHCID 574776664-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

생성물 1

HCID 866853107-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5(6H)-one수율 76%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

A flask was charged with 7-chloroimidazo[1,2-c]pyrimidin-5(6H)-one (Preparation H, 1.02 g, 6.00 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (Preparation E, 3.24 g, 9.00 mmol), K3PO4 (2.55 g, 12.0 mmol) and XPHOS (0.572 g, 1.20 mmol). Degassed iPrOH (24 mL) and degassed H2O (2 mL) were added and the suspension was sonicated for 1-2 minutes. The mixture was purged with N2 for 10 minutes with vigorous mixing and Pd2dba3 (0.549 g, 0.600 mmol) was added. The mixture was heated at reflux under an N2 atmosphere for 24 hours and was cooled to ambient temperature. The mixture was diluted with EtOAc (20 mL) and was sonicated for 5 minutes. The suspension was filtered through a packed Celite plug (EtOAc elution) and concentrated to give an orange, oily solid. The solid was treated with Et2O and was stirred until a granular suspension formed. The solid was collected, washed with Et2O and H2O and dried in vacuum to give the title compound (1.51 g, 76% yield) as a light tan powder. MS (apci) m/z=332.3 (M+H).

후처리

  1. customDegassed iPrOH (24 mL) and degassed H2O (2 mL)
  2. additionwere added
  3. customthe suspension was sonicated for 1-2 minutes
  4. customThe mixture was purged with N2 for 10 minutes
  5. additionwith vigorous mixing
  6. temperatureThe mixture was heated
  7. temperatureat reflux under an N2 atmosphere for 24 hours
  8. customwas sonicated for 5 minutes
  9. filtrationThe suspension was filtered through a packed Celite plug (EtOAc elution)
  10. concentrationconcentrated
  11. customto give an orange, oily solid
  12. customformed
  13. customThe solid was collected
  14. washwashed with Et2O and H2O
  15. customdried in vacuum

출처 및 근거

ORD 기록
ord-8be0b7c51ee44b8986e3584f66ed646a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962596B2

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