Hydrochloric Acid → HCID 11824456, compound

HRID 1940165Notes

Reaction equation

HRID 1940165 reaction equation
CN(CCN(C)C)C.[Li]CCCC.[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].[CH3:25][O:26][C:27]1[CH:32]=[C:31]([O:33][CH3:34])[N:30]=[C:29](C(OCC=C)=O)[N:28]=1.Cl.C1C[O:45][CH2:44]C1>C1CCCCC1.CO>[Cl:14][C:15]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]2[C:16]=1[C:17]([C:29]1[N:28]=[C:27]([O:26][CH3:25])[CH:32]=[C:31]([O:33][CH3:34])[N:30]=1)([OH:19])[O:18][C:44]2=[O:45]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 57842,5-Dichlorobenzoic acidHCID 8028Tetrahydrofuran3×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 21466110HCID 21466110, compoundHCID 178418339Butyllithium

Product 1

HCID 11824456HCID 11824456, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of 1.22 g of TMEDA and 60 ml of THF is prepared under anhydrous condition and cooled to -10° with stirring. 36.03 g of a 20.5% solution of n-BuLi in cyclohexane is added and after 30 mins stirring the solution is cooled to -60°. A solution of 10.0 g of 2,5-dichlorobenzoic acid in 40 ml of THF is added over 10 min. at -60°. After a further 30 mins of stirring this solution is added over 15 min under argon pressure to a solution of 8.97 g of allyl 4,6-dimethoxypyrimidine-2-carboxylate in 60 ml of THF at -25° and the clear yellow solution cooled to -25°. After stirring at -20° for 60 mins, 60 ml of 10% HCl are added and the temperature allowed to rise to 13° with stirring over a 15 min period. The organic phase is separated and evaporated to yield a viscous residue to which is added 17 ml of methanol. The resulting suspension is cooled in an ice/water bath, filtered and the crystals washed with 2×10 ml methanol and dried under vacuum at 70° C. to yield the title product.

Workup

  1. customis prepared under anhydrous condition
  2. temperaturecooled to -10°
  3. stirringstirring the solution
  4. temperatureis cooled to -60°
  5. stirringAfter a further 30 mins of stirring this solution
  6. temperaturethe clear yellow solution cooled to -25°
  7. stirringAfter stirring at -20° for 60 mins
  8. customto rise to 13°
  9. stirringwith stirring over a 15 min period
  10. customThe organic phase is separated
  11. customevaporated
  12. customto yield a viscous residue to which
  13. temperatureThe resulting suspension is cooled in an ice/water bath
  14. filtrationfiltered
  15. washthe crystals washed with 2×10 ml methanol
  16. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-c5267a21aa9042f3bc381de0c76e7a13
Source dataset
uspto-grants-1997_12
Patent number
US05698694

Reaction notes

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