Sodium hydride → HCID 66668642, compound

HRID 871143Notes

Reaction equation

HRID 871143 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].Cl[C:9]1[C:14]([I:15])=[CH:13][N:12]=[CH:11][N:10]=1.[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[I:15][C:14]1[C:9]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[N:10][CH:11]=[N:12][CH:13]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 112302044-Chloro-5-iodopyrimidineHCID 178418936HCID 178418936, compound

Product 1

HCID 66668642HCID 66668642, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-1,2,3-triazole (63.2 mg, 0.915 mmol) in THF (Volume: 2411 μl), was added portion wise at 0° C., NaH (39.9 mg, 0.998 mmol). The reaction mixture was stirred at that temperature for 30 min, then 4-chloro-5-iodopyrimidine (200 mg, 0.832 mmol) was added. The reaction mixture was allowed to warm to room temperature. To this solution was added saturated aqueous NH4Cl and the mixture was allowed to stir for 5 min at which time it was diluted with ethyl acetate and extracted 2×. The combined organics were washed with brine 1×. The organics were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (90 mg, 40%).

Workup

  1. stirringto stir for 5 min at which time it
  2. extractionextracted 2×
  3. washThe combined organics were washed with brine 1×
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6db8dfd15af54438ad14640f42938cd1
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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