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

HRID 1352744
ノート
印刷プレビュー

反応式

HRID 1352744 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-663deaf75d4f48c59bdc5b9c2568a29c
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07220736B2

反応ノート

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