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2-(Methylthio)-4-(trimethylstannyl)pyrimidine → 6-(2-Furyl)-5-[2-(methylthio)pyrimidin-4-yl]pyrazin-2-amine

HRID 1710694
Notes
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Reaction equation

HRID 1710694 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:13])=[N:6][C:7]=1[C:8]1[O:9][CH:10]=[CH:11][CH:12]=1.[CH3:14][S:15][C:16]1[N:21]=[C:20]([Sn](C)(C)C)[CH:19]=[CH:18][N:17]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.CN(C)C=O>[O:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:7]1[N:6]=[C:5]([NH2:13])[CH:4]=[N:3][C:2]=1[C:18]1[CH:19]=[CH:20][N:21]=[C:16]([S:15][CH3:14])[N:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 112662292-(Methylthio)-4-(trimethylstannyl)pyrimidineHCID 594576565-Bromo-6-(2-furyl)pyrazin-2-amine

Product 1

HCID 160716596-(2-Furyl)-5-[2-(methylthio)pyrimidin-4-yl]pyrazin-2-amineYield 47%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst
HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
150 °C

Procedure

A microwave oven reactor was charged with 5-bromo-6-furan-2-ylpyrazin-2-ylamine (Preparation 2, 220 mg, 0.91 mmol), 2-methylsulfanyl-4-trimethylstannanylpyrimidine* (500 mg, 1.74 mmol), bis-(triphenylphosphin)palladium (II) chloride (60 mg, 0.08 mmol) and dimethylformamide (2.5 mL). The mixture was heated at 150° C. for 10 min in the microwave oven, then cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (dichloromethane to dichloromethane/methanol 95:5) gave the title compound as a yellowish solid (123 mg, 47%). *Prepared according to Sandosham J.; Undheim, K. Tetrahedron 1994, 50 (1), 275-284.

Workup

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate
  3. extractionthe aqueous phase extracted twice with ethyl acetate
  4. washthe organic layers washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-5a9cc99e8adb4eaca29c6fafc30b2455
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07790728B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes