1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 4-Amino-2-(2-phthalimidoethylthio)pyrimidine

HRID 34797

Reaction equation

HRID 34797 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[S:3].Br[CH2:10][CH2:11][N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22].N12CCCNC1C=CCCC2>CN(C)C=O>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]=[C:2]([S:3][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[N:4]=1

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 150726561,2,3,4,6,7,8,10A-octahydropyrimido[1,2-a]azepineHCID 178507915HCID 178507915, compound

Product 1

HCID 212987374-Amino-2-(2-phthalimidoethylthio)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-thiocytosine (0.51 g.), dimethylformamide (5 ml.), N-(2-bromoethyl)phthalimide (1.12 g.) and 1,8-diazabicyclo[5,4,0]undec-5-ene (0.67 g.) was stirred at room temperature for 6 hours and then evaporated to dryness. The residue was stirred with a mixture of water and ethyl acetate and the insoluble material collected to give 4-amino-2-(2-phthalimidoethylthio)pyrimidine which was used without further purification.

Workup

  1. customevaporated to dryness
  2. stirringThe residue was stirred with a mixture of water and ethyl acetate
  3. customthe insoluble material collected

Sources & evidence

ORD record
ord-8ce077abc7b747369a5f93591d8d0d13
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

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