Phosphorus tribromide → 6-Benzyloxy-3-[2-(4-bromomethyl-phenyl)-ethyl]-3H-pyrimidin-4-one

HRID 564164Notes

Reaction equation

HRID 564164 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:27].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][Br:27])=[CH:19][CH:18]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 670074186-Benzyloxy-3-[2-(4-hydroxymethyl-phenyl)-ethyl]-3H-pyrimidin-4-one

Product 1

HCID 670072886-Benzyloxy-3-[2-(4-bromomethyl-phenyl)-ethyl]-3H-pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 200 mg (0.60 mmol) 6-benzyloxy-3-[2-(4-hydroxymethyl-phenyl)-ethyl]-3H-pyrimidin-4-one (example 20.1a) in 2.0 mL of DCM is added at 0° C. 29 μL (0.30 mmol) phosphorus tribromide. The mixture is stirred 2 h at RT and is then added to 5% aqueous NaHCO3-solution. The layers are separated, the aqueous phase is extracted with DCM and the organic phase is washed with water. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated to afford the product.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with DCM
  3. washthe organic phase is washed with water
  4. dry with materialThe combined organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customto afford the product

Sources & evidence

ORD record
ord-6dfde11f38694d449e29368efc2cc452
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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