Water → Guanine

HRID 1371278Notes

Reaction equation

HRID 1371278 reaction equation
[CH:1]1[NH:2][C:3]2[N:9]=[C:8]([NH2:10])[N:7]=[C:6](Cl)[C:4]=2[N:5]=1.C(N(CC)CC)C.C[O:20]C1C=C(C)C(S)=CC=1.O>CO>[NH:7]1[C:6](=[O:20])[C:4]2[NH:5][CH:1]=[N:2][C:3]=2[N:9]=[C:8]1[NH2:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27595964-Methoxy-2-methylthiophenolHCID 1785084356-chloro-1H-purin-2-amine

Product 1

HCID 135398634Guanine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloroguanine derivative prepared in Preparation 6 (4.86 g) was dissolved in 85 ml of methanol and 1.4 g of triethylamine and 2.9 g of 4-methoxythiocresol were added. The reaction mixture was reacted under reflux condition for 24 hours. The reaction was stopped by adding 20 ml of water, and the methanol was removed by distillation under reduced pressure. The reaction mixture was extracted with dichloromethane and purified by silica gel column to give a compound wherein 6-position of guanine was substituted by 4-methoxyphenylthio group.

Workup

  1. customThe reaction mixture was reacted
  2. temperatureunder reflux condition for 24 hours
  3. customthe methanol was removed by distillation under reduced pressure
  4. extractionThe reaction mixture was extracted with dichloromethane
  5. custompurified by silica gel column

Sources & evidence

ORD record
ord-84d17f4f92b641489ef262c6b1c5cfc1
Source dataset
uspto-grants-2007_01
Patent number
US07157448B2

Reaction notes

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