Sodium hydride → HCID 59580029, compound

HRID 2279622Notes

Reaction equation

HRID 2279622 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][NH:7][N:6]=1.Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1>C1COCC1>[CH3:3][O:4][C:5]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]([C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 178469941HCID 178469941, compound

Product 1

HCID 59580029HCID 59580029, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 528 mg, 13.2 mmol) is added portion wise to a solution of ethyl 3-methoxy-1H-pyrazole-4-carboxylate (1.5 g, 8.81 mmol) in 40 mL of THF at RT. Evolution of H2 (g) is observed. After about 5-10 min, 2-chloropyrimidine (1.0 g, 8.81 mmol) is added, and the resulting reaction mixture is stirred at reflux for 15 h. After cooling to RT, the reaction is quenched with 10 mL of sat. NH4Cl and 10 mL of water and extracted with CH2Cl2 (2×40 mL). The combined organic extracts are dried (Na2SO4), filtered, and evaporated in vacuo to give a brown solid. Purification by silica gel column chromatography (gradient from 50% EtOAc/hexane to EtOAc) affords the title compound as a fluffy white solid.

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 15 h
  3. customthe reaction is quenched with 10 mL of sat. NH4Cl and 10 mL of water
  4. extractionextracted with CH2Cl2 (2×40 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a brown solid
  9. customPurification by silica gel column chromatography (gradient from 50% EtOAc/hexane to EtOAc)

Sources & evidence

ORD record
ord-c32aa99dd9ea4cf2a172e384fef15345
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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