3-[5-chloro-2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamide → 5-chloro-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-6-(6-methyl-pyridin-2-ylmethoxy)-3H-pyrimidin-4-one

HRID 2172627Notes

Reaction equation

HRID 2172627 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][C:20]=2[CH3:21])[C:12](N(OC)C)=[O:13])[C:5]([CH3:22])=[N:4][C:3]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=1.[C:32]([Mg]Br)#[CH:33]>O1CCCC1>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([C:12](=[O:13])[C:32]#[CH:33])[CH:18]=[CH:19][C:20]=2[CH3:21])[C:5]([CH3:22])=[N:4][C:3]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=1

Participants

4

Reactant 2

HCID 715816383-[5-chloro-2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamideHCID 178418486HCID 178418486, compound

Product 1

HCID 715816375-chloro-2-methyl-3-(2-methyl-5-propynoyl-phenyl)-6-(6-methyl-pyridin-2-ylmethoxy)-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-[5-chloro-2-methyl-4-(6-methyl-pyridin-2-ylmethoxy)-6-oxo-6H-pyrimidin-1-yl]-N-methoxy-4,N-dimethyl-benzamide from Step B (73 mg, 0.16 mmol) in tetrahydrofuran (2 mL), cooled using an ice water bath, was added ethynylmagnesium bromide, 0.5M in tetrahydrofuran, (0.5 mL, 0.25 mmol) in a drop-wise manner. Additional Grignard reagent was added as necessary to ensure full product formation. After thirty minutes, the reaction was quenched into ice cold water and extracted with ethyl acetate. The organic layer was washed with saturated ammonium chloride, water and brine and dried over magnesium sulfate. The slurry was filtered and concentrated. The crude material was used without any additional purification.

Workup

  1. waitAfter thirty minutes
  2. customthe reaction was quenched into ice cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated ammonium chloride, water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe slurry was filtered
  7. concentrationconcentrated
  8. customThe crude material was used without any additional purification

Sources & evidence

ORD record
ord-da899bcd7ca043f4bc3b68ca47526a3c
Source dataset
uspto-grants-2015_06
Patent number
US09056110B2

Reaction notes

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