Morpholine → HCID 86711769, compound

HRID 528496Notes

Reaction equation

HRID 528496 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH3:20])[CH2:8][CH2:9][O:10][C:11]1[C:12](Cl)=[N:13][C:14]([Cl:18])=[N:15][C:16]=1[Cl:17])([CH3:4])([CH3:3])[CH3:2].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6](=[O:21])[N:7]([CH2:8][CH2:9][O:10][C:11]1[C:16]([Cl:17])=[N:15][C:14]([Cl:18])=[N:13][C:12]=1[N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[CH3:20])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86711768HCID 86711768, compound

Product 1

HCID 86711769HCID 86711769, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl-[2-(2,4,6-trichloro-pyrimidin-5-yloxy)-ethyl]-carbamic acid tert-butyl ester (1.50 mmol), morpholine (130 μL, 1.50 mmol) and triethylamine (417 μL, 3.00 mmol) in ethanol (5 mL) was stirred at RT for 1 hour 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 [2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester (quantitative). LCMS: RT=3.89 min, [M-CH2CH2NMeBoc+H]+=250/252/254.

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-238b917eb7f84c80b19d813c5b1060d8
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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