Tetrahydrofuran → HCID 21715625, compound

HRID 1387220Notes

Reaction equation

HRID 1387220 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([S:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=O)[N:4]=1.[C:21]([O:24][CH2:25][CH2:26][N+:27]#[C-:28])(=O)[CH3:22].C1CCN2C(=NCCC2)CC1.C1C[O:43]CC1>>[CH2:21]([O:24][C:25]([C:26]1[N:27]=[CH:28][O:16][C:14]=1[C:13]1[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=1[S:11][C:5]1[N:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=1)=[O:43])[CH3:22]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27362212-[(4,6-Dimethoxypyrimidin-2-yl)sulfanyl]benzoic acidHCID 10176119HCID 10176119, compound

Product 1

HCID 21715625HCID 21715625, compound

Conditions

Temperature
45 °C

Procedure

2 g (4,6-dimethoxypyrimidine-2-ylthio)benzoic acid was dissolved in THF, and the solution was added while stirring with 1.22 g N,N′-carbonyldiimidazole at room temperature. The mixture was them stirred for 50 min. at 40-50° C. The solution reacted was fed dropwise while stirring into THF solution of 1.55 g isocyanoethyl acetate at −5° C., immediately after dropping of 2 g DBU at −15° C., and the resulting solution was stirred for two nights at room temperature. After completing the reaction, the solution reacted was poured into ice water, stirred for 30 min. and then extracted with a mixed-solvent consisting of ether and ethyl acetate. The organic layer obtained was washed with water and saturated saline solution in turn and was then dried by using anhydrous magnesium sulfate, and then, the solvent used was removed by distillation under reduced pressure. The residue obtained was purified by using silica gel column chromatography, affording the objective substance in an amount of 1.36 g.

Workup

  1. additionthe solution was added
  2. customThe solution reacted
  3. stirringthe resulting solution was stirred for two nights at room temperature
  4. customthe reaction
  5. customthe solution reacted
  6. stirringstirred for 30 min.
  7. extractionextracted with a mixed-solvent
  8. customThe organic layer obtained
  9. washwas washed with water and saturated saline solution in turn
  10. customwas then dried
  11. customthe solvent used was removed by distillation under reduced pressure
  12. customThe residue obtained
  13. customwas purified
  14. customaffording the objective substance in an amount of 1.36 g

Sources & evidence

ORD record
ord-ee7c3ec2c1064acc822ccdcf2eaf5f4a
Source dataset
uspto-grants-2001_07
Patent number
US06268310B1

Reaction notes

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