Hexamethyldisilazane → HCID 58203538, compound

HRID 2194810Notes

Reaction equation

HRID 2194810 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([C:13]2[NH:14][C:15](=[O:22])[NH:16][C:17](=[O:21])[C:18]=2[CH2:19][CH3:20])[C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C[Si](C)(C)N[Si](C)(C)C.[CH2:32]([O:34][CH2:35]Cl)[CH3:33].Cl[Sn](Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>Cl[Si](C)(C)C>[CH3:8][C:6]1[CH:5]=[C:4]([N:9]([C:13]2[N:14]([CH2:35][O:34][CH2:32][CH3:33])[C:15](=[O:22])[NH:16][C:17](=[O:21])[C:18]=2[CH2:19][CH3:20])[C:10](=[O:12])[CH3:11])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

7

Reactant 5

HCID 13838HexamethyldisilazaneHCID 18523Chloromethyl ethyl etherHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 21303242HCID 21303242, compound

Product 1

HCID 58203538HCID 58203538, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6397ChlorotrimethylsilaneCatalyst

Procedure

A mixture of N-(3,5-dimethyl-phenyl)-N-(5-ethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-acetamide (109) (301 mg, 1 mmol), hexamethyldisilazane (5 mL), and chlorotrimethylsilane (5 drops) was refluxed for 4 hr. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was dissolved in acetonitrile (5 mL). Chloromethyl ethyl ether (110 μL, 1.2 mmol) and SnCl4 (1 M in dichloromethane, 100 μL, 0.1 mmol) were added. The mixture was stirred at room temperature for 16 hrs. Excess sodium bicarbonate was then added and the mixture was stirred for 1 hr. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1)) to afford 162 mg (45%) of a white solid. m.p. 182-183° C.; HRMS (EI) Calcd. 359.184507. Found 359.183174.

Workup

  1. temperaturewas refluxed for 4 hr
  2. customthe mixture was evaporated in vacuo
  3. dissolutionThe residue was dissolved in acetonitrile (5 mL)
  4. stirringthe mixture was stirred for 1 hr
  5. customThe mixture was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:1))

Sources & evidence

ORD record
ord-a9b1c65a19234f34a4cbfcb05fc004c1
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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