Potassium Acetate → 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

HRID 2039716Notes

Reaction equation

HRID 2039716 reaction equation
Br[C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])[O:25][BH:24][O:23]1.C([O-])(=O)C.[K+]>COCCOC.Cl[Pd]Cl>[CH3:21][C:22]1([CH3:29])[C:26]([CH3:28])([CH3:27])[O:25][B:24]([C:2]2[C:10]3[CH:9]=[N:8][CH:7]=[N:6][C:5]=3[N:4]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:3]=2)[O:23]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 693027235-bromo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 693263825-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-7-tosyl-7h-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

As shown in FIG. 1—step iv, a mixture of compound 1004 (140 mg, 0.40 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane dimer (121 mg, 0.477 mmol), PdCl2 dppf2 (16 mg, 0.02 mmol) and potassium acetate (117 mg, 1.19 mmol) in 2 mL of DME were microwaved at 150° C. for 10 minutes. The reaction mixture was filtered through a short pad of silica gel with 30% EtOAc-70% hexanes as eluent to provide, after concentration to dryness, 158 mg (98%) of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, compound 1005: ESMS M+1=317.07.

Workup

  1. customwere microwaved at 150° C. for 10 minutes
  2. filtrationThe reaction mixture was filtered through a short pad of silica gel with 30% EtOAc-70% hexanes as eluent
  3. customto provide
  4. concentrationafter concentration to dryness, 158 mg (98%) of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine, compound 1005

Sources & evidence

ORD record
ord-29ce55c2466449108ec3d0a54439b081
Source dataset
uspto-grants-2013_11
Patent number
US08580802B2

Reaction notes

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