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Cesium fluoride → 4-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine

HRID 1812398
Notes
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Reaction equation

HRID 1812398 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)[C:5]([F:8])=[N:6][CH:7]=1.[F-].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([Sn](CCCC)(CCCC)[C:58]([O:60][CH2:61][CH3:62])=[CH2:59])CCC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1.CN(C=O)C>[CH2:61]([O:60][C:58]([C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[N:10]=2)[C:5]([F:8])=[N:6][CH:7]=1)=[CH2:59])[CH3:62]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 25953Cesium fluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 666118184-(5-Chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine

Product 1

HCID 666118404-(5-(1-Ethoxyvinyl)-2-fluoropyridin-3-YL)-6-methyl-1,3,5-triazin-2-amine
Yield 99%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 4-(5-chloro-2-fluoropyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (1.34 g, 5.59 mmol) was added DMF (8 mL), dioxane (48 mL), cesium fluoride (2.55 g, 16.78 mmol), X-Phos (0.258 g, 0.559 mmol), palladium (II) acetate (0.126 g, 0.559 mmol), and tributyl(1-ethoxyvinyl)stannane (2.64 mL, 7.83 mmol) (Aldrich), and the resulting mixture was stirred at 110° C. for 1.5 h. The reaction mixture was cooled to ambient temperature and purified via flash chromatography (neutral alumina) with 100% DCM (to remove the stannane), then 100% EtOAc to give the title compound (>99% yield). m/z (ESI, +ve ion) 276.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. custompurified via flash chromatography (neutral alumina) with 100% DCM (
  3. customto remove the stannane), then 100% EtOAc

Sources & evidence

ORD record
ord-2a55369fc038457c88e842f37c745f17
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08362241B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes