Triethylamine → 2,4-Dichloro-pyrimidine-5-carboxylic acid (2,2,2-trifluoro-ethyl)-amide

HRID 38046

Reaction equation

HRID 38046 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9](Cl)=[O:10])=[CH:4][N:3]=1.[F:12][C:13]([F:17])([F:16])[CH2:14][NH2:15].C(N(CC)CC)C>C(Cl)Cl>[F:12][C:13]([F:17])([F:16])[CH2:14][NH:15][C:9]([C:5]1[C:6]([Cl:8])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 137841122,4-Dichloropyrimidine-5-carbonyl chloride

Product 1

HCID 866647582,4-Dichloro-pyrimidine-5-carboxylic acid (2,2,2-trifluoro-ethyl)-amideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

2,4-Dichloropyrimidine-5-carbonyl chloride (1 g, 5 mmol) was dissolved in CH2Cl2 (20 mL), 2,2,2-trifluoroethylamine (515 mg, 5 mmol) and triethylamine (1.31 mL, 9 mmol) were added. The reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was purified by flash chromatography to yield a white solid (780 mg, 60%). MS: m/z=271.9 [M−H]−.

Workup

  1. customThe reaction mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-e3e74a819e39477187627512570c9e67
Source dataset
uspto-grants-2013_09
Patent number
US08524710B2

Linked notes

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