N-bromobutanimide → 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-bromo-4-hydroxy-6-methylpyridin-2(1H)-one

HRID 1866995Notes

Reaction equation

HRID 1866995 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[CH:11][C:10]2=[O:17])=[CH:6][N:5]=[C:4]([CH3:18])[N:3]=1.C1C(=O)N([Br:26])C(=O)C1>C(O)(=O)C>[NH2:1][C:2]1[C:7]([CH2:8][N:9]2[C:14]([CH3:15])=[CH:13][C:12]([OH:16])=[C:11]([Br:26])[C:10]2=[O:17])=[CH:6][N:5]=[C:4]([CH3:18])[N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 547242141-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-hydroxy-6-methylpyridin-2(1H)-one

Product 1

HCID 547241661-[(4-amino-2-methylpyrimidin-5-yl)methyl]-3-bromo-4-hydroxy-6-methylpyridin-2(1H)-oneYield 72.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-hydroxy-6-methylpyridin-2(1H)-one (0.5 g, 0.002 mol), and NBS (0.4 g, 0.002 mol)in glacial acetic acid (5.0 ml) was stirred at room temperature for 1 h under argon atmosphere. Acetic acid was removed in vacuo, residue was triturated with EtOAc containing 10% EtOH, and filtered. The pale yellow precipitate was washed with EtOAc containing 10% EtOH and dried in vacuo to afford the title compound (0.47 g, 725) as a pale yellow powder:

Workup

  1. customAcetic acid was removed in vacuo, residue
  2. customwas triturated with EtOAc containing 10% EtOH
  3. filtrationfiltered
  4. washThe pale yellow precipitate was washed with EtOAc containing 10% EtOH
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d5d5e4ab67814bb7a156f824cf6f1554
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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