Dichloromethane → HCID 53997340, compound

HRID 354011Notes

Reaction equation

HRID 354011 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:5][N:4]=1.ON1[C:24]2C=CC=[CH:28][C:23]=2N=N1.[ClH:29].CN(C)[CH2:32][CH2:33][CH2:34][N:35]=C=NCC.[CH2:41]([Cl:43])Cl>>[Cl:29][C:23]1[CH:28]=[C:33]([CH:32]=[C:41]([Cl:43])[CH:24]=1)[CH2:34][NH:35][C:9]([C:7]1[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=1)=[O:11]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23512552HCID 23512552, compound

Product 1

HCID 53997340HCID 53997340, compoundYield 85%

Procedure

To a solution of 1.2 g (4.6 mmol) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid in 30 ml CH2Cl2 1.28 ml (9.2 mmol) triethylamine, 0.62 g (4.6 mmol) 1-hydroxy-benzotriazole and 0.88 g (4.6 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride 1.05 g (6 mmol) 3,5-dichlorobenzylamine were added. The reaction mixture was stirred for 16 hrs. The reaction mixture was diluted with 20 ml CH2Cl2, washed with 50 ml 0.5N HCl and 50 ml H2O. The aqueous layers were back extracted with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 100:1) to give 1.64 g (85%) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid 3,5-dichloro-benzylamide as a colorless foam, MS (ISP): 418.1, 420.1 (M+H+).

Workup

  1. washwashed with 50 ml 0.5N HCl and 50 ml H2O
  2. extractionThe aqueous layers were back extracted with 50 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-a9bb4de2f6de453aacbb38a7f6edcb5f
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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