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Citric Acid → 4-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

HRID 917590
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HRID 917590 반응식
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([O:22]CC)=[O:21])=[CH:5][N:4]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>CS(C)=O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([OH:22])=[O:21])=[CH:5][N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22025927Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

생성물 1

HCID 226655724-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매
2회

실험 절차

2-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (prepared in Example 67-(1)) 2.00 g is suspended in dimethyl sulfoxide 10 ml, and the suspension is treated with a 10% aqueous sodium hydroxide solution 10 ml. The reaction mixture is still in suspension even 6 hours later. After addition of dimethyl sulfoxide 5 ml the mixture is stirred at room temperature over night. The resulting clear reaction solution is acidified with citric acid. The excess water (about 50 ml) is added thereto and resulting precipitate is filtered, washed with isopropylalcohol and then isopropyl ether, and concentrated in vacuo to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-carboxypyrimidine as a pale yellow impalpable powder, 1.864 g.

후처리

  1. customis still in suspension even 6 hours
  2. customresulting precipitate
  3. filtrationis filtered
  4. washwashed with isopropylalcohol
  5. concentrationisopropyl ether, and concentrated in vacuo

출처 및 근거

ORD 기록
ord-73964931de3a42feae9ff90b028884a4
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07273868B2

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