Thiourea → HCID 178508225, compound

HRID 614932Notes

Reaction equation

HRID 614932 reaction equation
[NH2:1][C:2](N)=[S:3].[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH2:15][O:16][CH2:17][CH2:18][O:19]C(=O)C2C=CC=CC=2)=C(Cl)N=1>C(O)(C)C>[OH:19][CH2:18][CH2:17][O:16][CH2:15][N:12]1[CH:11]=[N:10][C:9]2[C:2](=[S:3])[NH:1][C:6]([NH2:5])=[N:14][C:13]1=2

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 137857472-Amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine

Product 1

HCID 178508225HCID 178508225, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Thiourea (0.28g) was added to a refluxing solution of 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (1.27g) in isopropanol (40ml). The reaction mixture was heated at reflux for 11/2 hours and then chilled. 9-(2-benzoyloxyethoxymethyl)thioguanine (0.58g, m.p. 199°-202° C.) was removed by filtration. This was added to 40ml of aqueous ammonia (about 7N) and the mixture heated on a stream bath for 10 minutes and then stirred overnight at room temperature. The water and ammonia were removed in vacuo and the residue triturated with acetone and then with ether to remove benzamide. The remaining solid was recrystallized twice from water to give yellow flakes of 9-(2-hydroxyethoxymethyl)thioguanine (0.26g., m.p. 251°-254° C.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 11/2 hours
  3. temperaturechilled
  4. custom9-(2-benzoyloxyethoxymethyl)thioguanine (0.58g, m.p. 199°-202° C.) was removed by filtration
  5. additionThis was added to 40ml of aqueous ammonia (about 7N)
  6. temperaturethe mixture heated on a stream bath for 10 minutes
  7. customThe water and ammonia were removed in vacuo
  8. customthe residue triturated with acetone
  9. customwith ether to remove benzamide
  10. customThe remaining solid was recrystallized twice from water

Sources & evidence

ORD record
ord-ffd7f64d4b0341e4b59a34176b0c4d0a
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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