Dichloromethane → HCID 9959819, compound

HRID 354006Notes

Reaction equation

HRID 354006 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:14][N:13]=[C:12]([CH2:23]OS(C)(=O)=O)[N:11]=1)=[O:9].C(Cl)Cl>O>[F:35][C:33]([F:36])([F:34])[C:31]1[CH:30]=[C:5]([CH:4]=[C:3]([C:2]([F:38])([F:37])[F:1])[CH:32]=1)[CH2:6][N:7]([CH3:29])[C:8]([C:10]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[CH:14][N:13]=[C:12]([CH2:23][NH:11][CH2:10][CH2:8][N:7]([CH3:29])[CH3:6])[N:11]=1)=[O:9]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 54027074HCID 54027074, compound

Product 1

HCID 9959819HCID 9959819, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 0.62 g (1.07 mmol) methanesulfonic acid 4-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-5-(2-chloro-phenyl)-pyrimidin-2-ylmethyl ester in 10 ml CH2Cl2 0.29 ml (2.66 mmol) 2-dimethylyminoethylamine were added. The reaction mixture was stirred for 16 hrs. at RT and than 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/NH4OH 110:10:1) to give 0.22 g (36%) 5-(2-chloro-phenyl)-2-[(2-dimethylamino-ethylamino)-methyl]-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless oil, MS (ISP): 574.1 (M+H+).

Workup

  1. extractionextracted three times with 50 ml CH2Cl2
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH/NH4OH 110:10:1)

Sources & evidence

ORD record
ord-085bd693089045f7a1cd51b83296b3c3
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

Loading…