Tetrahydrofuran → HCID 66321152, compound

HRID 871141Notes

Reaction equation

HRID 871141 reaction equation
[NH:1]1[CH:5]=N[CH:3]=[N:2]1.[H-].[Na+].Cl[C:9]1[C:14]([I:15])=[CH:13][N:12]=[CH:11][N:10]=1.[CH2:16]1COCC1>C(Cl)Cl>[I:15][C:14]1[C:9]([N:1]2[CH:5]=[CH:16][CH:3]=[N:2]2)=[N:10][CH:11]=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 66321152HCID 66321152, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1H-1,2,4-triazole (0.158 g, 2.288 mmol) in THF (Volume: 6.03 ml) cooled to 0° C. was added NaH (0.100 g, 2.496 mmol). The reaction mixture was stirred for 30 min at this temperature and then 4-chloro-5-iodopyrimidine (0.500 g, 2.080 mmol) was added. The reaction mixture was allowed to warm to room temperature. After 16 hr, reaction quenched with saturated aqueous NH4Cl and diluted with EtOAc. The aqueous and organic layers were separated. Aqueous phase was extracted with EtOAc (3×). The organics layers were combined, dried over Na2SO4, filtered, and concentrated to afford an orange residue. The crude material was dissolved in a minimal amount of CH2Cl2 to be chromatographed. Purification of the crude material by silica gel chromatography using an ISCO machine (40 g column, 40 mL/min, 20-80% EtOAc in hexanes over 20 min, tr=13 min) gave 5-iodo-4-(1H-pyrazol-1-yl)pyrimidine (113 mg, 20%) as a white solid.

Workup

  1. waitAfter 16 hr
  2. customreaction
  3. customquenched with saturated aqueous NH4Cl
  4. additiondiluted with EtOAc
  5. customThe aqueous and organic layers were separated
  6. extractionAqueous phase was extracted with EtOAc (3×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford an orange residue
  11. customto be chromatographed
  12. customPurification of the crude material by silica gel chromatography
  13. customan ISCO machine (40 g column, 40 mL/min, 20-80% EtOAc in hexanes over 20 min, tr=13 min)

Sources & evidence

ORD record
ord-b6c51b5d595a44968348f071394b625e
Source dataset
uspto-grants-2015_03
Patent number
US08969586B2

Reaction notes

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