Sodium Carbonate → HCID 21934644, compound

HRID 1241398Notes

Reaction equation

HRID 1241398 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([CH3:15])[N:9]=2)=[N:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)(C)C>[CH3:15][C:10]1[N:9]=[C:8]([NH:7][C:5]2[S:6][C:2]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[CH:3][N:4]=2)[CH:13]=[C:12]([CH3:14])[N:11]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 21934606HCID 21934606, compound

Product 1

HCID 21934644HCID 21934644, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

To a round bottomed flask were added (5-bromo-thiazol-2-yl)-(2,6-dimethyl-pyrimidin-4-yl)-amine (23-3) (100 mg, 0.35 mmol), 4-pyridineboronicacid (47 mg, 0.39 mmol), and isopropanol. After 0.5 hour palladium acetate (0.1 mg 0.0035 mmol), triphenylphosphine (2.75 mg, 0.0105 mmol), sodiumcarbonate (45 mg, 0.42 mmol) and water were added. The reaction was heated under reflux for 1.0 hour. The reaction was cooled, solvents removed and the residue dissolved into methanol (4.0 mL). Trifluoroacetic acid (0.5 mL) was added and the mixture purified by reverse phase preparative HPLC (C18) giving the above compound as a TFA salt. 1H-NMR (400 MHz, CD3OD) 8.71 (2H, br-s), 8.48 (1H, s), 8.18 (2H, br-s), 6.99 (1H, s), 2.82 (3H, s), 2.57 (3H, s). MS(M+1)=284.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1.0 hour
  3. temperatureThe reaction was cooled
  4. customsolvents removed
  5. dissolutionthe residue dissolved into methanol (4.0 mL)
  6. additionTrifluoroacetic acid (0.5 mL) was added
  7. customthe mixture purified by reverse phase preparative HPLC (C18)

Sources & evidence

ORD record
ord-7a7fecb7f6fa4f2bb414a8d9b74bc488
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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