Isopropanol → 4-Amino-1-benzylpyrimidin-2(1H)-one

HRID 538231Notes

Reaction equation

HRID 538231 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[OH-].CC(O)C.[NH:23]1[CH:30]=[CH:29][C:27]([NH2:28])=[N:26][C:24]1=[O:25].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CO.CN(C=O)C>[NH2:28][C:27]1[CH:29]=[CH:30][N:23]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24](=[O:25])[N:26]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 7498Benzyl BromideHCID 2723671Tetrabutylammonium HydroxideHCID 178418229Cytosine

Product 1

HCID 3085814-Amino-1-benzylpyrimidin-2(1H)-oneYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A 0.1 M solution of tetra-N-butylammonium hydroxide in a mixture of MeOH and 2-propanol (90 mL, 9.0 mmol) was added dropwise to a stirred suspension of cytosine (1 g, 9.0 mmol) in DMF (70 mL). The solution became clear and benzyl bromide (2.14 mL, 18 mmol) was added dropwise. The reaction mixture was stirred at RT for 2 hours and then the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM with a gradient of 0/100 to 50/50). The desired fractions were collected and the solvents evaporated in vacuo to yield 4-amino-1-benzyl-1H-pyrimidin-2-one (1 g, 57% yield) as a white solid.

Workup

  1. customthe solvents were evaporated in vacuo
  2. customThe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-dacb25459be944318f45a77abc92edcb
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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