Morpholine → (R)-2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propionic acid ethyl ester

HRID 528453Notes

Reaction equation

HRID 528453 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@H:5]([O:7][C:8]1[C:9](Cl)=[N:10][C:11]([Cl:15])=[N:12][C:13]=1[Cl:14])[CH3:6])[CH3:2].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(N(CC)CC)C>C(O)C>[CH2:1]([O:3][C:4](=[O:17])[C@H:5]([O:7][C:8]1[C:13]([Cl:14])=[N:12][C:11]([Cl:15])=[N:10][C:9]=1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86711739(R)-2-(2,4,6-Trichloro-pyrimidin-5-yloxy)-propionic acid ethyl ester

Product 1

HCID 86711740(R)-2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propionic acid ethyl esterYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (R)-2-(2,4,6-trichloro-pyrimidin-5-yloxy)-propionic acid ethyl ester (522 mg, 1.74 mmol), morpholine (152 μL, 1.74 mmol) and triethylamine (484 μL, 3.48 mmol) in ethanol (15 mL) was stirred at RT for 18 hours then partitioned between ethyl acetate and water. The aqueous phase was extracted with further ethyl acetate and the combined organic extracts dried (Na2SO4) and concentrated in vacuo affording (R)-2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propionic acid ethyl ester (490 mg, 80%). LCMS: RT=3.57 min, [M+H]+=350/352.

Workup

  1. customthen partitioned between ethyl acetate and water
  2. extractionThe aqueous phase was extracted with further ethyl acetate
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62a115b11489465b8eec5388415c6a21
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

Loading…