Sodium hydride → HCID 5329387, compound

HRID 1241361Notes

Reaction equation

HRID 1241361 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[H-].[Na+].Br[C:11]1[S:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][N:15]=1>C1COCC1>[C:16]1([C:13]2[S:12][C:11]([NH:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][N:3]=3)=[N:15][CH:14]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 689584-AminopyrimidineHCID 107287232-Bromo-5-phenylthiazole

Product 1

HCID 5329387HCID 5329387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-aminopyrimidine (30 mg, 0.32 mmol) was dissolved in 1 mL anhydrous THF in a flame dried flask under Ar. Sodium hydride (6 mg, 60% dispersion, 0.2 mmol) was then added to the flask at room temperature. When the bubbling stopped, 2-bromo-5-phenylthiazole (50 mg, 0.21 mmol) was added and the reaction was heated to reflux overnight. The solvent was removed under reduced pressure, water was added, and the resulting precipitate filtered. The compound was then dissolved in DMSO, purified by reverse phase preparative HPLC (C18), free-based with NaHCO3 (aq.), extracted with 3×DCM, and concentrated. 1H-NMR (300 MHz, DMSO-d6) 8.87 (1H, s), 8.47 (1H, d, J=5.6), 7.88 (1H, s), 7.63 (2H, d, J=7.1), 7.42 (2H, t, J=7.8), 7.29 (1H, t, J=7.6), 7.07 (1H, d, J=6.1). MS M+1=255.3. MP>250° C.

Workup

  1. customdried flask under Ar
  2. temperaturethe reaction was heated
  3. temperatureto reflux overnight
  4. customThe solvent was removed under reduced pressure, water
  5. additionwas added
  6. filtrationthe resulting precipitate filtered
  7. dissolutionThe compound was then dissolved in DMSO
  8. custompurified by reverse phase preparative HPLC (C18), free-based with NaHCO3 (aq.)
  9. extractionextracted with 3×DCM
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-48fce16cf8b74b03a23b43ad7486938e
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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