LY 43578 → 8-Chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidine

HRID 622096Notes

Reaction equation

HRID 622096 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)O)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>CS(O)(=O)=O>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:8]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[C:10]3[CH:11]=[N:12][CH:13]=[N:14][C:15]=32)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 161536LY 43578HCID 516892Sodium Bicarbonate

Product 1

HCID 1339698-Chloro-5-(4-chlorophenyl)-5H-indeno[1,2-d]pyrimidineYield 51.6%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 4.0 g of α, α-bis(4-chlorophenyl)-5-pyrimidinemethanol in 25 ml of methanesulfonic acid was stirred under a nitrogen atmosphere for 18 hours. The solution was poured into a sodium bicarbonate solution and extracted with ethyl acetate. The organic extract was washed with a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. Recrystallization from ethyl acetate/isooctane provided 1.95 g of the desired title product, m.p. 158°-163° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with a saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from ethyl acetate/isooctane

Sources & evidence

ORD record
ord-3062b5ac0c8f4c61b46a4a5e9c1310c1
Source dataset
uspto-grants-1988_09
Patent number
US04769378

Reaction notes

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