Water → 2-[3-(3-Methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 33976Notes

Reaction equation

HRID 33976 reaction equation
CO[N:3]([C:9]1[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[C:11]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[N:10]=1)[CH2:4][C:5](NC)=[O:6].[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[CH2:38][Mg]Cl.O.C(OCC)(=O)C>C1COCC1>[CH3:33][O:34][C:35]1[CH:36]=[C:37]([CH2:38][C:5](=[O:6])[CH2:4][NH:3][C:9]2[N:14]([CH3:15])[C:13](=[O:16])[C:12]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)=[C:11]([C:27]3[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=3)[N:10]=2)[CH:41]=[CH:42][CH:43]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 865966512-(N'-methoxy-N'-methylaminocarbonylmethylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-oneHCID 178490222HCID 178490222, compound

Product 1

HCID 115840062-[3-(3-Methoxy-phenyl)-2-oxo-propylamino]-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(N′-methoxy-N′-methylaminocarbonylmethylamino)-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (400 mg, 0.93 mmol) in THF (10 mL) at 0° C. was slowly added 3-methoxybenzylmagnesium chloride (Rieke Metal, 0.25 M in THF, 20 mL). After 3 h, water (100 mL) and ethyl acetate (200 mL) were added. The layers were separated. The organic layer was washed with brine (3×80 mL), dried, and evaporated to give crude product. Column chromatograph purification (silica gel, 1-2% MeOH/CH2Cl2) gave the product as a solid. M+1=491.2.

Workup

  1. customat 0° C.
  2. customThe layers were separated
  3. washThe organic layer was washed with brine (3×80 mL)
  4. customdried
  5. customevaporated
  6. customto give crude product
  7. customColumn chromatograph purification (silica gel, 1-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9de89b760f4e45b097447bda49d0264a
Source dataset
uspto-grants-2008_09
Patent number
US07429594B2

Reaction notes

Loading…