Sodium hydride → 3-[(2,6-Bis-benzyloxy-5-ethyl-pyrimidin-4-yl)-cyano-methyl]-5-methyl-benzonitrile

HRID 426118Notes

Reaction equation

HRID 426118 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([CH2:23][CH3:24])=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[C:32]#[N:33])#[N:27].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([CH:28]([C:26]#[N:27])[C:29]2[CH:30]=[C:31]([CH:34]=[C:35]([CH3:37])[CH:36]=2)[C:32]#[N:33])[C:12]([CH2:23][CH3:24])=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 596868662,4-Bis-benzyloxy-6-chloro-5-ethyl-pyrimidineHCID 667054463-(Cyanomethyl)-5-methylbenzonitrile

Product 1

HCID 591847833-[(2,6-Bis-benzyloxy-5-ethyl-pyrimidin-4-yl)-cyano-methyl]-5-methyl-benzonitrileYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2,4-Bis-benzyloxy-6-chloro-5-ethyl-pyrimidine (39) (9.89 g, 27.87 mmol) and 3-Cyanomethyl-5-methyl-benzonitrile (4.15 g, 26.55 mmol) in anhydrous DMF (50 ml) in an ice-water bath under an atmosphere of nitrogen, was portionwise added 60% sodium hydride (2.34 g, 58.4 mmol). After stirring for 1 hr, the mixture was stirred at room temperature for overnight. The mixture was neutralized with aqueous saturated ammonium chloride solution. The crude product was extracted with ether and recrystallized from dichloromethane-hexane to afford 10.3 g (82%) a pale yellow solid; m.p. 139-141° C.; 1H NMR (200 MHz, CDCl3) δ: 1.00 (3H, t, J=7.6 Hz), 2.37 (3H, s), 2.52-2.58 (2H, m), 5.29 (1H, s), 5.49 (4H, s), 7.27-7.50 (10H, m); m/z (EI): 474 (M+).

Workup

  1. stirringthe mixture was stirred at room temperature for overnight
  2. extractionThe crude product was extracted with ether
  3. customrecrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-d874b035b3b34936b68593e1d9ae39e0
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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