Cesium carbonate → HCID 86679614, compound

HRID 577668Notes

Reaction equation

HRID 577668 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:19][C:20]2[CH:21]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=[CH:24][CH:25]=2)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[CH3:34][N:35]([CH3:44])[CH2:36][CH2:37][N:38]1[CH:42]=[C:41]([NH2:43])[CH:40]=[N:39]1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.[Cl-].[Na+].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]>[C:29]([O:28][C:27](=[O:33])[NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[N:7]=[C:2]([NH:43][C:41]3[CH:40]=[N:39][N:38]([CH2:37][CH2:36][N:35]([CH3:44])[CH3:34])[CH:42]=3)[N:3]=2)[CH:21]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 283739571-(2-(Dimethylamino)ethyl)-1H-pyrazol-4-amineHCID 86679612tert-butyl (3-((2-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)phenyl)carbamate

Product 1

HCID 86679614HCID 86679614, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of tert-butyl {3-[(2-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}carbamate (300 mg, 0.61 mmol) in 1,4-dioxane (4 mL) in a microwave vial was added 1-[2-(dimethylamino)ethyl]-1H-pyrazol-4-amine (94.1 mg, 0.61 mmol) followed by Cs2CO3 (298 mg, 0.915 mmol), Pd2(dba)3 (8.2 mg, 0.009 mmol) and Xantphos (5.4 mg, 0.009 mmol) and the mixture heated in the microwave to 140° C. for 45 min. The reaction was cooled to rt and brine (20 mL) was added and the mixture was extracted with EtOAc (three×10 mL). The combined extracts were dried over MgSO4, filtered and stripped to give the title compound as a dark oil that was taken on to the next step with no purification. m/z (ESI+) for C30H44N8O4Si 609.25 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to rt
  2. extractionthe mixture was extracted with EtOAc (three×10 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-343c49ba68d946238ebe8bda71a4f65b
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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