Dimethylamine → HCID 53785342, compound

HRID 650629Notes

Reaction equation

HRID 650629 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12][C:13]([CH2:16]OS(C)(=O)=O)=[N:14][CH:15]=1)=[O:9].[CH3:38][NH:39][CH3:40].O>C(Cl)Cl.C(O)C>[F:34][C:32]([F:33])([F:35])[C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:31]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:11]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[N:12][C:13]([CH2:16][N:39]([CH3:40])[CH3:38])=[N:14][CH:15]=1)=[O:9]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 54354681HCID 54354681, compound

Product 1

HCID 53785342HCID 53785342, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.40 g (0.73 mmol) methanesulfonic acid 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-phenyl-pyrimidin-2-ylmethyl ester in 5 ml CH2Cl2 1 ml 5.6 m dimethylamin-solution in ethanol were added. The reaction mixture was stirred for 16 hrs. at RT. The reaction mixture was poured into H2O and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 20:1) to give 0.33 g (90%) 2-dimethylaminomethyl-4-phenyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless oil, MS (ISP): 497.2 (M+H+).

Workup

  1. customat RT
  2. extractionextracted three times 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 20:1)

Sources & evidence

ORD record
ord-d820d3492dd74415bfe272cbc560ffb6
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

Loading…