Tributylstannane → HCID 66915568, compound

HRID 656488Notes

Reaction equation

HRID 656488 reaction equation
Br[C:2]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:3]=1[O:4][CH2:5][C:6]1[C:7]2[CH:8]=[N:9][CH:10]=[N:11][C:12]=2[CH2:13][CH2:14][CH:15]=1.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:2]2[C:6]3([CH2:5][O:4][C:3]=2[CH:16]=1)[CH2:15][CH2:14][CH2:13][C:12]1[N:11]=[CH:10][N:9]=[CH:8][C:7]3=1

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 57468507HCID 57468507, compound

Product 1

HCID 66915568HCID 66915568, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1 mmol of 5-(2-bromo-5-methoxyphenoxymethyl)-7,8-dihydroquinazoline, 0.5 mmol of azoisobutyronitrile (AIBN) and 1.5 mmol of tributyltin hydride in 50 ml of benzene is heated at reflux for 1-2 hours. The reaction solution is concentrated and the residue is taken up in diethyl ether. The solution is admixed with 1M NaOH and stirred vigorously at room temperature for 1 hour. The phases are separated and the organic phase is washed with 1M sodium hydroxide solution and brine, dried with sodium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. temperatureat reflux for 1-2 hours
  2. concentrationThe reaction solution is concentrated
  3. customThe phases are separated
  4. washthe organic phase is washed with 1M sodium hydroxide solution and brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-400dcc0f82ab45e9bd22477b0311c292
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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