Bromine → 5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione

HRID 1912354Notes

Reaction equation

HRID 1912354 reaction equation
[C:1]([C:9]1[C:10](=[O:19])[N:11]([CH3:18])[C:12](=[O:17])[N:13]([CH3:16])[C:14]=1[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:20]Br>C(Cl)(Cl)Cl>[C:1]([C:9]1[C:10](=[O:19])[N:11]([CH3:18])[C:12](=[O:17])[N:13]([CH3:16])[C:14]=1[CH2:15][Br:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 8023085-benzoyl-1,3,6-trimethyl-2,4(1H,3H)-Pyrimidinedione

Product 1

HCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dioneYield 57.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(See, e.g., Tsupak et al., Khimiya Geterotsiklicheskikh Soedinenii. 7:1096-1102 (2003); Tsupak et al., Russ. Chem. Bull. 55:2265-2270 (2006)). To a solution of 3 (2.61 g, 10.1 mmol) in chloroform (13 mL) was added bromine (1.62 g, 0.52 mL, 20.3 mmol in 3 mL chloroform) dropwise over 30 min at room temperature. The reaction mixture was further stirred for 1 min at room temperature before concentrated in vacuo. The crude reaction mixture was purified by flash chromatography to yield 4 (1.96 g, 57%); mp 164-167° C.; MS (ES+) (m/z): [M+1]+ calculated for C14H14BrN2O3, 338.18. found 337.15, 338.93. This compound matched analytical data as reported (see, e.g., Tsupak et al., Khimiya Geterotsiklicheskikh Soedinenii., supra; Tsupak et al., Russ. Chem. Bull., supra).

Workup

  1. concentrationbefore concentrated in vacuo
  2. customThe crude reaction mixture
  3. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-d9cfd0e3aeaa46eda34828f4e69f3f7b
Source dataset
uspto-grants-2013_12
Patent number
US08609661B2

Reaction notes

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