Sodium → N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-(3-dimethylaminopropenoyl)-6-methylpyrimidinamine

HRID 1251506Notes

Reaction equation

HRID 1251506 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[N:12]([CH2:23][CH3:24])[C:13]1[N:18]=[C:17]([C:19](=[O:21])[CH3:20])[CH:16]=[C:15]([CH3:22])[N:14]=1>CO>[Br:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:10])[CH3:11])[CH:6]=[CH:5][C:4]=1[N:12]([CH2:23][CH3:24])[C:13]1[N:18]=[C:17]([C:19](=[O:21])[CH:20]=[CH:4][N:12]([CH3:23])[CH3:13])[CH:16]=[C:15]([CH3:22])[N:14]=1

Participants

4

Reactant 2

HCID 5360545Sodium2×HCID 18323676N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-acetyl-6-methylpyrimidinamine

Product 1

HCID 53660591N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-(3-dimethylaminopropenoyl)-6-methylpyrimidinamineYield 121.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (0.08 g, 3.5 mmol) was added to methanol (20 mL) with stirring. After the sodium reacted, a solution of N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-acetyl-6-methyl-pyrimidinamine (1.0 g, 2.67 mmol) in methanol (5 mL) was added and the reaction mixture was stirred for 5 min. Gold's reagent ((dimethylaminomethyleneaminomethylene))dimethyl-ammonium chloride (0.66 g, 4 mmol) was added and stirring was continued for 19 h. The reaction mixture was concentrated in vacuo; the residue was dissolved in chloroform and the solution was washed with a saturated NaHCO3 solution, dried over MgSO4 and filtered solvent removal in vacuo gave a brown solid, which upon trituration with hexanes afforded N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-(3-dimethylaminopropenoyl)-6-methylpyrimidinamine as a yellow solid (700 mg): NMR (CDCl3, 300 MHz): 7.9-7.65 (br s, 1H), 7.5 (s, 1H), 7.25-7.2 (m, 2H), 7.15 (s, 1H), 6.1-5.8 (br s, 1H), 4.3-4.15 (m, 1H), 3.9-3.75 (m, 1H), 3.2-3.0 (br s, 3H), 3.0-2.85 (m, 1H), 2.8-2.6 (br s, 3H), 2.5-2.3 (br s, 3H), 1.35-1.2 (m, 9H): CI-MS, 431, 433 (M+H).

Workup

  1. stirringthe reaction mixture was stirred for 5 min
  2. stirringstirring
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutionthe residue was dissolved in chloroform
  5. washthe solution was washed with a saturated NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvent removal in vacuo
  9. customgave a brown solid, which upon trituration with hexanes

Sources & evidence

ORD record
ord-9141082180bc42209092e492cb9e0d0e
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

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