Sodium hydride → 8-((3-fluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)benzyl)oxy)-1-isopropyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 920394Notes

Reaction equation

HRID 920394 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:19][OH:20])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1.Cl[C:22]1[CH:34]=[C:26]2[N:27]([CH:31]([CH3:33])[CH3:32])[CH2:28][CH2:29][CH2:30][N:25]2[C:24](=[O:35])[N:23]=1.[H-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[N:11][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:13][CH:14]=1)[CH2:19][O:20][C:22]1[CH:34]=[C:26]2[N:27]([CH:31]([CH3:32])[CH3:33])[CH2:28][CH2:29][CH2:30][N:25]2[C:24](=[O:35])[N:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66825479(3-Fluoro-4-((6-(trifluoromethyl)-3-pyridinyl)oxy)phenyl)methanolHCID 717434708-Chloro-1-isopropyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

Product 1

HCID 712367308-((3-fluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)benzyl)oxy)-1-isopropyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-fluoro-4-((6-(trifluoromethyl)pyridin-3-yl)oxy)phenyl)methanol (126 mg, 0.439 mmol) and 8-chloro-1-isopropyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (20 mg, 0.088 mmol) in N,N-dimethylformamide (DMF) (8 mL), was added NaH (35.1 mg, 0.878 mmol) 25 and stirred for 1 h at rt. The reaction mixture was quenched by addition of sat. aq. NH4Cl solution and was filtered. The solution was purified by MDAP to afford the desired product as a white solid.

Workup

  1. customThe reaction mixture was quenched by addition of sat. aq. NH4Cl solution
  2. filtrationwas filtered
  3. customThe solution was purified by MDAP

Sources & evidence

ORD record
ord-3cd8ef917e7f4acf92430c8da2ad1ae5
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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