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

HRID 528448Notes

Reaction equation

HRID 528448 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[C:8](Cl)=[N:9][C:10]([Cl:14])=[N:11][C:12]=1[Cl:13])[CH3:2].[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(N(CC)CC)C>>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[C:12]([Cl:13])=[N:11][C:10]([Cl:14])=[N:9][C:8]=1[N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH3:2]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86711734(2,4,6-Trichloro-pyrimidin-5-yloxy)-acetic acid ethyl ester

Product 1

HCID 86711735(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl esterYield 95%

Procedure

A mixture of (2,4,6-trichloro-pyrimidin-5-yloxy)-acetic acid ethyl ester (2.67 g, 9.35 mmol), morpholine (815 μL, 9.35 mmol) and triethylamine (2.6 mL, 18.7 mmol) in IMS (50 mL) was stirred at RT for 2 hours before the reaction was concentrated in vacuo. The resultant residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with further ethyl acetate and the combined organic extracts dried (Na2SO4) and concentrated in vacuo affording (2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-acetic acid ethyl ester (2.97 g, 95%). LCMS: RT=3.35 min, [M+H]+=336/338/340.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe resultant residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with further ethyl acetate
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4dd6be735b58456f80206d81ee03ce64
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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