Propargyl bromide → HCID 136087680, compound

HRID 1722698Notes

Reaction equation

HRID 1722698 reaction equation
[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:14][NH:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[C:8]=2[CH3:13])[N:3]=1.Br[CH2:29][C:30]#[CH:31].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(O)C.CO>[NH2:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:14][N:15]([CH2:31][C:30]#[CH:29])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[C:8]=2[CH3:13])[N:3]=1

Participants

7

Reactant 3

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 136100139HCID 136100139, compound

Product 1

HCID 136087680HCID 136087680, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A suspension of 0.10 g (0.27 mmol) of 2-amino-5-methyl-6-[[(3,4,5-trimethoxyphenyl)amino]methyl]-4(3H)-quinazolinone, (see Example P) 0.54 ml (2.7 mmol) of an 80% solution of 3-bromo-1-propyne in toluene, and 0.42 ml (3.0 mmol) of triethylamine in 10 ml of ethanol is heated under reflux for eighteen hours. The solution is cooled, concentrated, and combined with material obtained from a similar experiment also using 0.10 g of starting material. The residue is dissolved in methanol and treated with 10 g of flash silica gel. The methanol is evaporated and the powder is applied to a column of 100 g of flash silica gel packed in dichloromethane/methanol (50:1). Elution with the same solvent initially, gradually increasing the polarity to dichloromethane/methanol (10:1) gives 0.07 g of a glassy material. Two recrystallizations from ethanol gives 0.0196 g (8.5%) of the product as an off-white solid, mp 202°-204° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for eighteen hours
  3. temperatureThe solution is cooled
  4. concentrationconcentrated
  5. customobtained from a similar experiment
  6. additiontreated with 10 g of flash silica gel
  7. customThe methanol is evaporated
  8. washElution with the same solvent initially
  9. temperaturegradually increasing the polarity to dichloromethane/methanol (10:1)

Sources & evidence

ORD record
ord-54e3552561d14345b8cd218627e1b3eb
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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