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Triethylamine → (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine

HRID 917597
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반응식

HRID 917597 반응식
CS[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]([CH:20]=[O:21])=[CH:5][N:4]=1.Cl[C:23]1[CH:28]=CC=[C:25]([C:29]([O:31]O)=O)[CH:24]=1.C([N:35](CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[OH:31][CH2:29][C@@H:25]1[CH2:24][CH2:23][CH2:28][N:35]1[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]([CH:20]=[O:21])=[CH:5][N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 220259362-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine

생성물 1

HCID 86587299(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine

시약·촉매·용매 2

HCID 6212Chloroform용매
HCID 8857
Ethyl Acetate
용매

실험 절차

A solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine (prepared in Example 84-(2)) 2.057 g in chloroform 20 ml is treated at 0° C. for 30 minutes with m-chloroperbenzoic acid (80%) 1.468 g. L-(S)-Prolinol 0.901 g and then triethylamine 1.33 ml are added thereto. The reaction is carried out at 0° C. for 1 hour. The reaction mixture is elevated to room temperature, diluted with ethyl acetate, washed with an aqueous sodium hydrogen carbonate solution, water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The precipitate is filtered off and the filtrate is concentrated in vacuo to give (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine as a colorless amorphous, 1.9990 g. MS(m/z): 377(M+H)+

후처리

  1. customis elevated to room temperature
  2. washwashed with an aqueous sodium hydrogen carbonate solution, water
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  4. filtrationThe precipitate is filtered off
  5. concentrationthe filtrate is concentrated in vacuo

출처 및 근거

ORD 기록
ord-bb0e8ad1c05e4fdab933616e49b0b118
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07273868B2

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