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

HRID 426130Notes

Reaction equation

HRID 426130 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]([C:23]([CH3:26])([CH3:25])[CH3:24])=[C:11](Cl)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]([C:30]1[CH:31]=[C:32]([CH2:37][C:38]#[N:39])[CH:33]=[C:34]([CH3:36])[CH:35]=1)#[N:29].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([CH:37]([C:38]#[N:39])[C:32]2[CH:31]=[C:30]([CH:35]=[C:34]([CH3:36])[CH:33]=2)[C:28]#[N:29])[C:12]([C:23]([CH3:26])([CH3:25])[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 591848352,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidineHCID 667054463-(Cyanomethyl)-5-methylbenzonitrile

Product 1

HCID 591847533-[(2,6-Bis-benzyloxy-5-tert-butyl-pyrimidin-4-yl)-cyano-methyl]-5-methyl-benzonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2,4-Bis-benzyloxy-5-tert-butyl-6-chloro-pyrimidine (3.8 g, 10 mmol) and 3-cyano-5-methylphenyl acetonitrile (1.56 g, 10 mmol) in anhydrous DMF (20 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (880 mg, 22 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ether and purified by silica gel column chromatography (eluent, EA:hexanes (1:10)) to afford 1.48 g (30%) of the title compound as a colorless syrup. m.p. 126-128° C.; 1H NMR (200 MHz, CDCl3) δ 1.46 (9H, s), 2.36 (3H, s), 5.29 (1H, d, J=12.2 Hz), 5.38 (1H, d, J=12.2 Hz), 5.46 (2H, s), 5.98 (1H, s), 7.22-7.46 (10H, m); m/z (EI) 502 (M+).

Workup

  1. stirring, the mixture was further stirred at room temperature for overnight
  2. extractionthe crude product was extracted with ether
  3. custompurified by silica gel column chromatography (eluent, EA:hexanes (1:10))

Sources & evidence

ORD record
ord-40faf8a89ea84184966f7422221480de
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…