Sodium hydride → HCID 13631688, compound

HRID 2119165Notes

Reaction equation

HRID 2119165 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])=[N:10][CH:11]([CH3:15])[NH:12][C:13]=1[CH3:14])=[O:7])[CH2:2][CH2:3][CH3:4].[H-].[Na+].Cl[C:26]([O:28][CH2:29][CH:30]([CH2:35][CH3:36])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:27]>O1CCCC1>[CH2:1]([O:5][C:6]([C:8]1[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:10]([C:26]([O:28][CH2:29][CH:30]([CH2:35][CH3:36])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:27])[C:11]([CH3:15])=[N:12][C:13]=1[CH3:14])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 627832-Ethylhexyl chloroformateHCID 20191106HCID 20191106, compound

Product 1

HCID 13631688HCID 13631688, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.4 g of 5-(n-butyloxycarbonyl)-4-(2-chlorophenyl)-2,6-dimethyl-dihydropyrimidine in 10 ml of tetrahydrofuran was added at room temperature to a suspension of 1 g of sodium hydride (as 50% suspension) in 5 ml of tetrahydrofuran. After 20 minutes, a solution of 1 g of 2-ethylhexyl chloroformate in 5 ml of tetrahydrofuran was added dropwise and after 30 minutes the reaction solution was diluted with ice water and extracted three times with ether. The organic layer was washed twice with water and dried over anhydrous magnesium sulfate and evaporated to remove the solvent to obtain 2 g of the residue. It was purified on 50 g of silica gel by column chromatography and eluted with 0.5% methanol/chloroform to obtain 1.47 g (71% yiled) of title compound.

Workup

  1. extractionextracted three times with ether
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto remove the solvent

Sources & evidence

ORD record
ord-bc3aab1caf754bfe9a33b61f68f10770
Source dataset
uspto-grants-1987_07
Patent number
US04683234

Reaction notes

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