Benzyl Bromide → 1-benzyl-8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one

HRID 930800Notes

Reaction equation

HRID 930800 reaction equation
[Cl:1][C:2]1[CH:11]=[C:6]2[NH:7][CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:12])[N:3]=1.[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:7]1[CH2:8][CH2:9][CH2:10][N:5]2[C:4](=[O:12])[N:3]=[C:2]([Cl:1])[CH:11]=[C:6]12)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1357418828-Chloro-3,4-dihydro-1H-pyrimido[1,6-A]pyrimidin-6(2H)-one

Product 1

HCID 903039511-benzyl-8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-oneYield 46.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 8-chloro-3,4-dihydro-1H-pyrimido[1,6-a]pyrimidin-6(2H)-one (1 g, 2.32 mmol) and sodium hydride (0.28 g, 6.95 mmol) in N,N-dimethylformamide (10 mL) was added (bromomethyl)benzene (0.40 mL, 2.78 mmol) at room temperature, and stirred for 30 min at r.t. Purification via reverse phase column (0.3% TFA in water/acetonitrile) afforded the title compound (300 mg).

Workup

  1. customPurification via reverse phase column (0.3% TFA in water/acetonitrile)

Sources & evidence

ORD record
ord-cbdc7b93651045e6afec80baab99b81f
Source dataset
uspto-grants-2016_03
Patent number
US09296755B2

Reaction notes

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