Dichloromethane → 6-Methyl-5-[4-(2-furoyl)piperazin-1-ylmethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4689

Reaction equation

HRID 4689 reaction equation
Cl.Cl.[CH3:3][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:5]=1[CH2:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.ClCCl.[O:35]1[CH:39]=[CH:38][CH:37]=[C:36]1[C:40](Cl)=[O:41]>C(N(CC)CC)C>[CH3:3][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:5]=1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([C:40]([C:36]2[O:35][CH:39]=[CH:38][CH:37]=2)=[O:41])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 682422-Furancarbonyl chlorideHCID 201513906-Methyl-5-(1-piperazinylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine dihydrochloride

Product 1

HCID 201514026-Methyl-5-[4-(2-furoyl)piperazin-1-ylmethyl]-4-(3-nitrophenyl)-2-phenylpyrimidineYield 97.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 6-methyl-5-(1-piperazinylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine dihydrochloride (1 g), dichloromethane (10 ml) and triethylamine (0.48 g), was added 2-furoyl chloride (0.31 g) at 5° C. under ice cooling. After stirring for 1 hour at the same temperature, the reaction mixture was concentrated under reduced pressure. The residue was suspended in water and adjusted to pH=9 with aqueous saturated sodium hydrogen carbonate. The precipitate was collected by filtration, washed with water and dried in vacuo to give 6-methyl-5-[4-(2-furoyl)piperazin-1-ylmethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine (1.02 g).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-1b0e899e852c46f697084b105512427c
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Linked notes

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