Sodium hydride → 1-benzyl-8-((3,4-difluorobenzyl)oxy)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 930805Notes

Reaction equation

HRID 930805 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:21])[N:17]=[C:18](Cl)[CH:19]=[C:11]12)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:22][C:23]1[CH:24]=[C:25]([CH2:30][OH:31])[CH:26]=[CH:27][C:28]=1[F:29]>CN(C)C=O>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][N:12]2[C:16](=[O:21])[N:17]=[C:18]([O:31][CH2:30][C:25]3[CH:26]=[CH:27][C:28]([F:29])=[C:23]([F:22])[CH:24]=3)[CH:19]=[C:11]12)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5228333,4-Difluorobenzyl alcoholHCID 903039511-benzyl-8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

Product 1

HCID 771070321-benzyl-8-((3,4-difluorobenzyl)oxy)-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-oneYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (21.76 mg, 0.54 mmol) in N,N-dimethylformamide (DMF) (2 mL), 1-benzyl-8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (50 mg, 0.18 mmol) was added (3,4-difluorophenyl)methanol (0.026 mL, 0.22 mmol) at r.t., and stirred for 30 mins. The reaction mixture was quenched by water. Purification via reverse phase column (0.3% trifluoroacetate acid in acetonitrile/water) afforded the title compound (22 mg).

Workup

  1. customThe reaction mixture was quenched by water
  2. customPurification via reverse phase column (0.3% trifluoroacetate acid in acetonitrile/water)

Sources & evidence

ORD record
ord-6373d8d5fc494091a9e3e1f1b827fc9d
Source dataset
uspto-grants-2016_03
Patent number
US09296755B2

Reaction notes

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