Sodium Hydroxide → N-(1-Pyrazolylmethyl)-N-(4,6-dimethoxypyrimidin-5-yl)-chloroacetamide

HRID 542383Notes

Reaction equation

HRID 542383 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:13])[CH2:11][Cl:12])=[C:7]([O:14][CH3:15])[N:6]=[CH:5][N:4]=1.[NH:16]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[N:17]1.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[NH:16]1[CH:20]=[CH:19][C:18]([CH2:21][N:9]([C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[N:6][C:7]=2[O:14][CH3:15])[C:10](=[O:13])[CH2:11][Cl:12])=[N:17]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15585336N-(4,6-dimethoxypyrimidin-5-yl)chloroacetamideHCID 178478439HCID 178478439, compound

Product 1

HCID 178494238N-(1-Pyrazolylmethyl)-N-(4,6-dimethoxypyrimidin-5-yl)-chloroacetamide

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

347 g of N-(4,6-dimethoxypyrimidin-5-yl)-chloroacetamide, 60 g benzyltriethylammoniumchloride, 3 l CH2Cl2 and 252 g 1-pyrazolylmethylchloride are charged in a sulphonation flask and thereto added, quickly, 750 ml 30% aqueous NaOH (w/w) while cooling on a ice bath. The reaction temperature rises from 13° to 25°. The reaction mixture is further stirred under continued cooling on the ice bath until the temperature reaches 23°. Then the ice bath is removed and the reaction is stirred further for 2 hours. The reaction mixture is then diluted with 1.5 l of water and stirred. The organic phase is partitioned off, dried with Na2SO4 and filtered over a 6 cm SiO2 layer. The SiO2 -layer is washed with 10 l diethylether. The resulting reaction mixture is concentrated to 1.5 l and the precipitate, which has been falling out is filtered off and washed with pentane, then it is dried under vacuum at 50° to give the title compound m.p. 117°-119°.

Workup

  1. additionadded
  2. customrises from 13° to 25°
  3. customreaches 23°
  4. customThen the ice bath is removed
  5. stirringthe reaction is stirred further for 2 hours
  6. additionThe reaction mixture is then diluted with 1.5 l of water
  7. stirringstirred
  8. customThe organic phase is partitioned off
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered over a 6 cm SiO2 layer
  11. washThe SiO2 -layer is washed with 10 l diethylether
  12. customThe resulting reaction mixture
  13. concentrationis concentrated to 1.5 l
  14. filtrationthe precipitate, which has been falling out is filtered off
  15. washwashed with pentane
  16. customit is dried under vacuum at 50°

Sources & evidence

ORD record
ord-bd4ec9a30d4945c58370b9b115b932c8
Source dataset
uspto-grants-1987_04
Patent number
US04657579

Reaction notes

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