Sodium hydride → [3-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-acetonitrile

HRID 426191Notes

Reaction equation

HRID 426191 reaction equation
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:5]=[C:4]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:3]=1.[C:31]([SiH2:35][O:36][C:37]([CH3:48])([CH3:47])[C:38]1[CH:39]=[C:40]([CH2:44][C:45]#[N:46])[CH:41]=[CH:42][CH:43]=1)([CH3:34])([CH3:33])[CH3:32].[H-].[Na+]>CN(C=O)C>[C:31]([SiH2:35][O:36][C:37]([CH3:48])([CH3:47])[C:38]1[CH:39]=[C:40]([CH:44]([C:2]2[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:5]=[C:4]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[N:3]=2)[C:45]#[N:46])[CH:41]=[CH:42][CH:43]=1)([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 591847134-Chloro-5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidineHCID 178455425HCID 178455425, compound

Product 1

HCID 137328667[3-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-acetonitrileYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4-chloro-5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine (5.65 g, 13.17 mmol) and [3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-acetonitrile (3.27 g, 12.54 mmol) in anhydrous DMF (25 ml) in a water bath under a nitrogen atmosphere, was added 60% sodium hydride (1.0 g, 25.09 mmol). After 30 min., water bath was removed and the mixture was stirred for overnight at room temperature. The reaction mixture was neutralized with aqueous saturated ammonium chloride solution. The mixture was then partitioned between ether and water. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a yellow oil. The crude product was purified by silica gel column chromatography (eluent, EA:hexanes (1:15)) to afford 5.34 g (65%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 0.06 (6H, s), 0.90 (9H, s), 1.06 (6H, d, J=7.0 Hz), 3.01 (1H, m), 3.81 (6H, s), 4.71 (2H, s), 5.32 (2H, s), 5.35 (2H, s), 5.41 (3H, s), 6.86-6.91 (4H, m), 7.20-7.35 (6H, m), 7.41-7.49 (2H, m).

Workup

  1. customwater bath was removed
  2. customThe mixture was then partitioned between ether and water
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a crude product as a yellow oil
  8. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexanes (1:15))

Sources & evidence

ORD record
ord-6dbf3b9f3f3349f2aa7adc810c70e3a9
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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