Sodium hydride → HCID 71236725, compound

HRID 920392Notes

Reaction equation

HRID 920392 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.Cl[C:13]1[CH:23]=[C:17]2[N:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]2[C:15](=[O:24])[N:14]=1.[H-].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:13]2[CH:23]=[C:17]3[N:18]([CH3:22])[CH2:19][CH2:20][CH2:21][N:16]3[C:15](=[O:24])[N:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 697054-Methoxyphenethyl alcoholHCID 717434718-Chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

Product 1

HCID 71236725HCID 71236725, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-(4-methoxyphenyl)ethanol (183 mg, 1.202 mmol) and 8-chloro-1-methyl-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (200 mg, 1.002 mmol) in dimethyl sulfoxide (DMSO) (5 mL) stirred at room temp was added NaH (100 mg, 2.505 mmol) portionwise. The reaction mixture was stirred at room temp for 2 hr. The reaction was quenched with water and purified by prep-HPLC to give the title product as a white solid (150 mg).

Workup

  1. customThe reaction was quenched with water
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-f62cd931e95f40cb871b3d3dcc811535
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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