Triethylamine → 2-Chloro-4-(4-formylpiperazino)pyrimidine

HRID 1979944Notes

Reaction equation

HRID 1979944 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=[O:2].C(N(CC)CC)C.[Cl:16][C:17]1[N:22]=[C:21](Cl)[CH:20]=[CH:19][N:18]=1>C(O)C>[Cl:16][C:17]1[N:22]=[C:21]([N:6]2[CH2:7][CH2:8][N:3]([CH:1]=[O:2])[CH2:4][CH2:5]2)[CH:20]=[CH:19][N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 821911-Piperazinecarboxaldehyde

Product 1

HCID 138695702-Chloro-4-(4-formylpiperazino)pyrimidineYield 31.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Formylpiperazine (38.5 g) and triethylamine (34 g) in ethanol (500 ml) were added slowly to a stirred solution of 2,4-dichloropyrimidine (50 g) in ethanol (2.5 ml) at room temperature. The mixture was stirred at room temperature for 24 hours then evaporated in vacuo and the residue partitioned between chloroform and water. The organic phase was washed with water and the combined aqueous phases extracted with chloroform. The combined chloroform extracts were dried (Na2SO4), evaporated in vacuo and the residue was crystallized twice from ethyl acetate to give 2-chloro-4-(4-formylpiperazino)pyrimidine, (24 g), m.p. 125°-126° C.

Workup

  1. customthen evaporated in vacuo
  2. customthe residue partitioned between chloroform and water
  3. washThe organic phase was washed with water
  4. extractionthe combined aqueous phases extracted with chloroform
  5. dry with materialThe combined chloroform extracts were dried (Na2SO4)
  6. customevaporated in vacuo
  7. customthe residue was crystallized twice from ethyl acetate

Sources & evidence

ORD record
ord-b7a94321cbfc400694dc368fc88f9c81
Source dataset
uspto-grants-1984_11
Patent number
US04483859

Reaction notes

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