Triethylamine → 4-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine

HRID 917628노트

반응식

HRID 917628 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH2:6].C(N(CC)CC)C.[C:19]([C:22]1[C:23]([Cl:30])=[N:24][C:25]([Cl:29])=[N:26][C:27]=1Cl)([OH:21])=[O:20]>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][NH:6][C:27]1[C:22]([C:19]([OH:21])=[O:20])=[C:23]([Cl:30])[N:24]=[C:25]([Cl:29])[N:26]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 7380383-Chloro-4-methoxybenzylamineHCID 200839572,4,6-Trichloropyrimidine-5-carboxylic acid

생성물 1

HCID 178482874-(3-Chloro-4-methoxybenzylamino)-5-carboxy-2,6-dichloropyrimidine수율 91.6%

시약·촉매·용매 2

HCID 311Citric Acid용매HCID 6228Dimethylformamide용매2회

실험 절차

A N,N-dimethylformamide solution 6 ml of 3-chloro-4-methoxybenzylamine 1.51 g and triethylamine 2.46 g is dropped over a period of 25 minutes under ice cooling a solution of 5-carboxy-2,4,6-trichloropyrimidine (prepared in Example 318(1)) 2.00 g in N,N-dimethylformamide 12 ml, and the mixture is further stirred for 90 minutes. The reaction mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The combined extract is washed with water and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give 4-(3-chloro-4-methoxybenzylamino)-2,6-dichloropyrimidine-5-carboxylic acid as a pale brown crystalline powder 2.92 g. mp 144-151° C.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe combined extract
  3. washis washed with water
  4. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5fb491e0410846a882be6f0e025184bf
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273868B2

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