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

HRID 1352744Notes

Reaction equation

HRID 1352744 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.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

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 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-formylpyrimidine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-663deaf75d4f48c59bdc5b9c2568a29c
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

Loading…