Sulfuric Acid → 2-(5-Bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrile

HRID 2232060Notes

Reaction equation

HRID 2232060 reaction equation
C[O-].[Na+].[Na].[C:5]([CH2:7][C:8]([NH2:10])=[O:9])#[N:6].CO[C:13](=[N:25][C:26]([C:28]1[C:37]2[C:32](=[C:33]([Br:38])[CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)=O)[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.OS(O)(=O)=O>CO.O>[Br:38][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:32]=1[CH:31]=[CH:30][CH:29]=[C:28]2[C:26]1[NH:10][C:8](=[O:9])[C:7]([C:5]#[N:6])=[C:13]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[N:25]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7898CyanoacetamideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 19863963Methyl-N-(5-bromo-1-naphthoyl)-2-(1-naphthalenyl)acetimidate

Product 1

HCID 1358476532-(5-Bromo-1-naphthalenyl)-1,6-dihydro-4-[(1-naphthalenyl)methyl]-6-oxo-5-pyrimidinecarbonitrileYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of sodium methoxide, freshly prepared from sodium (1.5 g, 0.065 mol) in methanol (75 mL), was added cyanoacetamide (4.2 g, 0.050 mol). After 2 minutes, methyl-N-(5-bromo-1-naphthoyl)-2-(1-naphthalenyl)acetimidate (21.6 g, 0.050 mol) was added. The resulting mixture was stirred at room temperature for 15 hours, then heated to reflux for 4 hours. After cooling to room temperature, the mixture was neutralized with H2SO4 (1.8 mL) and diluted with water. The product was collected by filtration, washed with water, and dried in vacuo to give a yellow solid (16.4 g, 71%), which was used without purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling to room temperature
  4. filtrationThe product was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c3cfdf489d0542219c8935832ac1528f
Source dataset
uspto-grants-1988_11
Patent number
US04786640

Reaction notes

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