Dimethylamine → HCID 53854292, compound

HRID 354007Notes

Reaction equation

HRID 354007 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.[CH3:42][NH:43][CH3:44]>O>[F:34][C:33]([F:35])([F:36])[C:31]1[CH:30]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:37])[F:38])[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][N:43]([CH3:44])[CH3:42])[N:11]=1)=[O:9]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6344DichloromethaneHCID 54027074HCID 54027074, compound

Product 1

HCID 53854292HCID 53854292, compoundYield 70%

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 1.53 ml (8.52 mmol) of a 5.6 M solution of dimethylamine 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 200:10:1) to give 0.40 g (70%) 5-(2-chloro-phenyl)-2-dimethylaminomethyl-pyrimidine-4-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a colorless oil, MS (ISP): 531.1 (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 200:10:1)

Sources & evidence

ORD record
ord-e6c4d2977e284c99a9e90614cf821752
Source dataset
uspto-grants-2004_06
Patent number
US06756380B1

Reaction notes

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