2-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-N-methoxy-N-ethyl-acetamide → 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-one

HRID 528458Notes

Reaction equation

HRID 528458 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11](N(OC)CC)=[O:12])=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1.[CH3:24][Mg]Br>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:10][C:11](=[O:12])[CH3:24])=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1

Participants

4

Reactant 2

HCID 867117432-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-N-methoxy-N-ethyl-acetamideHCID 178418573HCID 178418573, compound

Product 1

HCID 867117441-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-N-methoxy-N-ethyl-acetamide (200 mg, 0.60 mmol) in THF (4 mL) at −78° C. was added methylmagnesium bromide (1.28 mL, 1.79 mmol, 1.4 M solution in THF/toluene) and the resulting mixture warmed to RT and stirred for 3 hours. The resulting mixture was quenched with 1M HCl and extracted with ethyl acetate. The combined organic extracts were washed with brine, then dried (Na2SO4) and concentrated in vacuo affording 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-propan-2-one as a white solid (146 mg, 80%). LCMS: RT=2.90 min, [M+H]+=306/308/310.

Workup

  1. customThe resulting mixture was quenched with 1M HCl
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13cf7600191b460b95ed5afb0fdc26c2
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

Loading…