Pyridine → HCID 57265491, compound

HRID 481422Notes

Reaction equation

HRID 481422 reaction equation
O[CH2:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:13][CH:12]=[CH:11][CH2:10]2)=[CH:5][N:4]=1.N1C=CC=CC=1.S(Cl)([Cl:27])=O>C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([C:9]1([C:6]2[CH:5]=[N:4][C:3]([CH2:2][Cl:27])=[N:8][CH:7]=2)[CH2:13][CH:12]=[CH:11][CH2:10]1)=[O:15])[CH3:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 19066275HCID 19066275, compound

Product 1

HCID 57265491HCID 57265491, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 1-(2-hydroxymethylpyrimidin-5-yl)cyclopent-3-ene carboxylate (5.0 g, 20.1 mmol), in chloroform (50 ml) was added pyridine (5.1 ml), followed by thionyl chloride (4.4 ml, 60.3 mmol). The reaction mixture was refluxed for 30 minutes, cooled to room temperature and quenched with water (50 ml). The chloroform layer was collected, washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic extract was dried over MgSO4 and then evaporated to an oily residue, which was purified by flashe chromatography with hexanes/ethyl acetate (3:1) as eluent.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. customquenched with water (50 ml)
  3. customThe chloroform layer was collected
  4. washwashed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. extractionThe organic extract
  6. dry with materialwas dried over MgSO4
  7. customevaporated to an oily residue, which
  8. customwas purified

Sources & evidence

ORD record
ord-a42482a1faf94a9e901e375ccdef8a49
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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