Potassium Carbonate → HCID 70142504, compound

HRID 1038862Notes

Reaction equation

HRID 1038862 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][CH2:12][C:13]([F:16])([F:15])[F:14])[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:17][Si:18]([CH3:34])([CH3:33])[CH2:19][CH2:20][O:21][CH2:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH2:32])[CH:30]=2)[CH:25]=[N:24]1.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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]>[F:14][C:13]([F:16])([F:15])[CH2:12][NH:11][C:4]1[C:5]2[O:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:2]([NH:32][C:29]2[CH:30]=[C:31]3[C:26]([CH:25]=[N:24][N:23]3[CH2:22][O:21][CH2:20][CH2:19][Si:18]([CH3:34])([CH3:33])[CH3:17])=[CH:27][CH:28]=2)[N:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 67293196HCID 67293196, compoundHCID 866651142-chloro-N-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidin-4-amine

Product 1

HCID 70142504HCID 70142504, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloro-N-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidin-4-amine (1.56 g, 6.20 mmol) and 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-amine (1.797 g, 6.82 mmol) were dissolved in 1,4-dioxane (10 mL). RuPhos (0.296 g, 0.620 mmol), Pd2dba3 (0.568 g, 0.620 mmol, Alfa) and K2CO3 (1.714 g, 12.40 mmol) were added. The tube was evacuated and purged with N2 (3×), and the mixture was heated at about 110° C. for about 5 h. The mixture was cooled to rt and filtered. The filter cake was washed with DCM (3×25 mL). The filtrate was washed with saturated aqueous NaCl (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 2:1 hexanes/EtOAc) to give N4-(2,2,2-trifluoroethyl)-N2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-6-yl)furo[3,2-d]pyrimidine-2,4-diamine (2.22 g, 75%): LC/MS (Table 2, Method h) Rt=2.26 min; MS m/z: 479 (M+H)+.

Workup

  1. customThe tube was evacuated
  2. custompurged with N2 (3×)
  3. temperatureThe mixture was cooled to rt
  4. filtrationfiltered
  5. washThe filter cake was washed with DCM (3×25 mL)
  6. washThe filtrate was washed with saturated aqueous NaCl (3×20 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography (silica gel, 2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-c3ecb862f1bf4089bcff185a0814cd35
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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