Thiourea → HCID 178508225, 화합물

HRID 614932노트

반응식

HRID 614932 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 178508225HCID 178508225, 화합물수율 29.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-ffd7f64d4b0341e4b59a34176b0c4d0a
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04146715

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