Triethylamine → Ethyl 4-((3-chloro-4-methoxy-phenyl)methylamino)-2-((2S)-2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate

HRID 2200907Notes

Reaction equation

HRID 2200907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9](S(C)=O)[N:8]=1.C(N(CC)CC)C.[NH:33]1[CH2:39][CH2:38][CH2:37][C@H:34]1[CH2:35][OH:36]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[CH2:5][NH:6][C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]([N:33]2[CH2:39][CH2:38][CH2:37][C@H:34]2[CH2:35][OH:36])[N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 640091L-ProlinolHCID 22665570Ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-(methylsulfinyl)pyrimidine-5-carboxylate

Product 1

HCID 52348789Ethyl 4-((3-chloro-4-methoxy-phenyl)methylamino)-2-((2S)-2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the solution of ethyl 4-((3-chloro-4-methoxybenzyl)amino)-2-methanesulfinyl-5-pyrimidine carboxylate in DCM was added triethylamine (4.24 g, 42 mmol). The mixture was cooled in an ice bath, then was added L-prolinol (2.2 g, 19.8 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 3 h. The reaction was monitored by LC-MS. After the completion of the reaction, the reaction mixture was washed with water, dilute hydrochloric acid, sodium bicarbonate aqueous solution and brine, each once. The organic phase was dried over sodium sulfate and concentrated until the solvent was removed. The product was used in subsequent procedures without further purification.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed with water, dilute hydrochloric acid, sodium bicarbonate aqueous solution and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated until the solvent
  6. customwas removed
  7. customThe product was used in subsequent procedures without further purification

Sources & evidence

ORD record
ord-999584349d1649d9b9b99a7f1263b864
Source dataset
uspto-grants-2016_06
Patent number
US09359371B2

Reaction notes

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