Triethylamine → HCID 53841856, compound

HRID 354008Notes

Reaction equation

HRID 354008 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.[CH2:19](N(CC)CC)C.ON1C2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.Cl.CN(C)[CH2:39][CH2:40][CH2:41][N:42]=[C:43]=NCC>C(Cl)Cl>[CH3:19][C:35]1[CH:30]=[C:40]([CH:39]=[C:33]([CH3:32])[CH:34]=1)[CH2:41][N:42]([CH3:43])[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

6

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23512552HCID 23512552, compound

Product 1

HCID 53841856HCID 53841856, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 0.30 g (1.15 mmol) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid in 20 ml CH2Cl2, 0.32 ml (2.3 mmol) triethylamine, 0.17 g (1.15 mmol) 1-hydroxy-benzotriazole and 0.22 g (1.15 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride 0.20 g (1.38 mmol) (3,5-dimethyl-benzyl)-methyl-amine were added. The reaction mixture was stirred for 16 hrs. The reaction mixture was 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) to give 0.36 g (79%) 2-methylsulfanyl-5-o-tolyl-pyrimidine-4-carboxylic acid (3,5-dimethyl-benzyl)-methyl-amide as a white foam, MS (EI): 391 (M+).

Workup

  1. additionwere added
  2. washThe reaction mixture was washed with 50 ml 0.5N HCl and 50 ml H2O
  3. extractionThe aqueous layers were back extracted with 50 ml CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-53c542240fa34467863fa457f519e184
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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