Dichloromethane → 2-Methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid (3,5-dimethyl-benzyl)-methyl-amide

HRID 650636Notes

Reaction equation

HRID 650636 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[C:6]([C:16]([OH:18])=O)=[CH:5][N:4]=1.ON1C2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2N=N1.Cl.CN(C)[CH2:32][CH2:33][CH2:34][N:35]=[C:36]=NCC.[CH2:41](Cl)Cl>>[CH3:41][C:28]1[CH:23]=[C:33]([CH:32]=[C:26]([CH3:25])[CH:27]=1)[CH2:34][N:35]([CH3:36])[C:16]([C:6]1[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:8][C:3]([S:2][CH3:1])=[N:4][CH:5]=1)=[O:18]

Participants

5

Reactant 4

HCID 6344Dichloromethane2×HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 217124342-Methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid

Product 1

HCID 537884882-Methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid (3,5-dimethyl-benzyl)-methyl-amideYield 82%

Procedure

To a solution of 2.60 g (9.99 mmol) 2-methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid in 70 ml CH2Cl2 2.78 ml (19.98 mmol) triethylamine, 1.34 g (9.99 mmol) 1-hydroxybenzotriazole and 1.91 g (9.99 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride 1.78 g (11.99 mmol) (3,5-dimethoxy-benzyl)-methyl-amine were added. The reaction mixture was stirred for 16 hrs. The reaction mixture was diluted with 100 ml CH2Cl2, washed with 100 ml 0.5N HCl and 100 ml H2O. The aqueous layers were backextracted with 100 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1) to give 3.20 g (82%) 2-methylsulfanyl-4-o-tolyl-pyrimidine-5-carboxylic acid (3,5-dimethyl-benzyl)-methyl-amide as a pale yellow oil, MS (EI): 391 (M+).

Workup

  1. washwashed with 100 ml 0.5N HCl and 100 ml H2O
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 40:1)

Sources & evidence

ORD record
ord-f7171ddf1ff44aaf84d1d91055a8d721
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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