Oxalyl chloride → Pyrimidine-5-carbonyl chloride

Participants

Reaction Steps

(±)-trans-2-Methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide was made following general procedure A, substituting pyrimidine-5-carbonyl chloride for 4-trifluoromethyl-benzoyl chloride. Pyrimidine-5-carbonyl chloride was prepared by reaction of pyrimidine-5-carboxylic acid with oxalyl chloride and dimethylformamide in methylene chloride. The crude 2-methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)ethyl-amide was isolated as a mixture of cis and trans isomers. Purification by silica gel chromatography (2% methanol/methylene chloride) yielded (±)-trans-2-methyl-1-(pyrimidine-5-carbonyl)-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid (4-chloro-phenyl)-ethyl-amide (44%). 1H-NMR (CDCl3) δ: 1.02-1.18 (m, 6H), 1.65-1.75 (m, 1H), 2.50-2.60 (m, 1H), 3.60-3.70 (m, 1H), 3.80 (q, 2H), 4.98-5.10 (m, 1H), 6.40 (d, 1H), 6.70 (d, 1H), 6.90-7.00 (m, 2H), 7.20 (d, 2H), 7.50 (d, 2H), 8.85 (s, 2H), 9.15 (s, 1H). MS m/z: 435/437 (M+1).

Provenance & Evidence