Triethylamine → 4-[4-(2,4-Dichloro-5-sulfamoylbenzoyl)piperazin-1-yl]-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine

HRID 4340Notes

Reaction equation

HRID 4340 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([CH3:17])[N:14]=[C:13]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[Cl:31][C:32]1[CH:40]=[C:39]([Cl:41])[C:38]([S:42](=[O:45])(=[O:44])[NH2:43])=[CH:37][C:33]=1[C:34](Cl)=[O:35]>C(Cl)(Cl)Cl>[Cl:31][C:32]1[CH:40]=[C:39]([Cl:41])[C:38]([S:42](=[O:44])(=[O:45])[NH2:43])=[CH:37][C:33]=1[C:34]([N:21]1[CH2:20][CH2:19][N:18]([C:13]2[CH:12]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:16]=[C:15]([CH3:17])[N:14]=2)[CH2:23][CH2:22]1)=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126038552,4-Dichloro-5-sulfamoylbenzoyl chlorideHCID 201523016-(3,4-Dimethoxyphenyl)-2-methyl-4-(1-piperazinyl)pyrimidine

Product 1

HCID 201522984-[4-(2,4-Dichloro-5-sulfamoylbenzoyl)piperazin-1-yl]-6-(3,4-dimethoxyphenyl)-2-methylpyrimidineYield 71.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 6-(3,4-dimethoxyphenyl)-2-methyl-4-(1-piperazinyl)pyrimidine (0.8 g) in chloroform (10 ml) were added triethylamine (0.39 ml) and 2,4-dichloro-5-sulfamoylbenzoyl chloride (0.74 g), and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was washed with water, dried over magnesium sulfate, and evaporated. The obtained mixture was chromatographed on silica gel eluting with chloroform-methanol mixture (49:1 v/v), to give 4-[4-(2,4-dichloro-5-sulfamoylbenzoyl)piperazin-1-yl]-6-(3,4-dimethoxyphenyl)-2-methylpyrimidine (1.03 g).

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customThe obtained mixture was chromatographed on silica gel eluting with chloroform-methanol mixture (49:1 v/v)

Sources & evidence

ORD record
ord-8713f1a083924a5fa46b8a31925ba557
Source dataset
uspto-grants-1988_02
Patent number
US04725600

Reaction notes

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