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

HRID 431052Notes

Reaction equation

HRID 431052 reaction equation
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.ClC1C=CC=C(C(OO)=O)C=1.[NH:33]1[CH2:39][CH2:38][CH2:37][C@H:34]1[CH2:35][OH:36].C(N(CC)CC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[OH:36][CH2:35][C@@H:34]1[CH2:37][CH2:38][CH2:39][N:33]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

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 640091L-ProlinolHCID 220259362-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine

Product 1

HCID 86587299(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidineYield 83.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine (2.057 g) in chloroform (20 ml) is treated with m-chloroperbenzoic acid (80%, 1.468 g) at 0° C. for 30 minutes. To the reaction mixture are is added L-prolinol (0.901 g), and then triethylamine (1.33 ml), and the mixture is reacted at 0° C. for one hour. The reaction mixture is warmed to room temperature, and diluted with ethyl acetate. The mixture is washed successively with a saturated aqueous sodium hydrogen carbonate solution, water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The precipitates are removed by filtration through a silica plug. The filtrate is concentrated under reduced pressure to give (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-formylpyrimidine (1.9990 g) as colorless amorphous, MS (m/z): 377 (MH+).

Workup

  1. washThe mixture is washed successively with a saturated aqueous sodium hydrogen carbonate solution, water
  2. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  3. customThe precipitates are removed by filtration through a silica plug
  4. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-bca2f8c666ec43599da2656054113172
Source dataset
uspto-grants-2003_12
Patent number
US06656935B2

Reaction notes

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