Potassium Carbonate → HCID 69430099, compound

HRID 854380Notes

Reaction equation

HRID 854380 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.C(B(CC)[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:8]2[C:4]3[N:5]=[CH:6][N:7]=[C:2]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[C:3]=3[CH:10]=[CH:9]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6428513-(Diethylboryl)pyridineHCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 69430099HCID 69430099, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [4 g, Reference Example 3] and diethyl-3-pyridyl-borane (2.1 g) in tetrahydrofuran (180 mL) was treated with palladium tetrakis triphenylphosphine (0.65 g) and potassium carbonate (3.59 g). The solution was stirred at reflux for 24 hours and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and brine. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure. The residue was subjected twice to flash column chromatography on silica eluting with a mixture of ethyl acetate and methanol (90:10, v/v) and a mixture of ethyl acetate and cyclohexane (50:50, v/v) to give the title compound (2.5 g) as an amorphous solid. MS: 351 [MH]+. LCMS (Method B) RT=3.05 minutes.

Workup

  1. temperatureat reflux for 24 hours
  2. customevaporated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and brine
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. additionThe residue was subjected twice to flash column chromatography on silica eluting with a mixture of ethyl acetate and methanol (90:10
  8. additionv/v) and a mixture of ethyl acetate and cyclohexane (50:50

Sources & evidence

ORD record
ord-bbac6baea07a432b9b8f8d51c624f6ae
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

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