Water → HCID 67354708, compound

HRID 1846171Notes

Reaction equation

HRID 1846171 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.[CH3:11][C:12](=O)[CH2:13][CH2:14][C:15](=O)[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Br:9][C:5]1[C:4]([CH3:10])=[N:3][C:2]([N:1]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:11])=[N:7][C:6]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80352,5-HexanedioneHCID 27377352-Amino-5-bromo-4,6-dimethylpyrimidine

Product 1

HCID 67354708HCID 67354708, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution containing 2.00 g (9.89 mmol) of 2-amino-5-bromo-4,6-dimethylpyrimidine in 16 mL of anhydrous toluene was added 1.36 mL (11.5 mmol) of 2,5-hexanedione followed by 96 mg (0.50 mmol) of p-toluenesulfonic acid. The reaction mixture was heated and stirred at reflux for 12 h. The reaction mixture was poured into 150 mL of water and then extracted with 200 mL of ethyl acetate. The organic solution was washed with 150 mL of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 5:1 hexanes-ethyl acetate afforded the expected product as light yellow crystals: yield 2.23 g (81%); mp 64-65° C.; silica gel TLC Rf 0.65 (6:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 2.34 (s, 6H), 2.67 (s, 6H) and 5.89 (s, 2H); 13C NMR (CDCl3) δ 14.5, 14.5, 24.9, 24.9, 108.7, 108.7, 118.6, 129.5, 129.5, 155.3, 155.3 and 166.9; mass spectrum (APCI), m/z 280.0458 (M+H)+ (C12H15N3Br requires 280.0449).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. extractionextracted with 200 mL of ethyl acetate
  4. washThe organic solution was washed with 150 mL of brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under diminished pressure
  7. customThe residue was purified by chromatography on a silica gel column (15×5 cm)
  8. washElution with 5:1 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-d28e345402f54f4292228aa430fe3dcc
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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