Thiourea → HCID 178508225、化合物

HRID 848086ノート

反応式

HRID 848086 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 178508225HCID 178508225、化合物収率 29.5%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Thiourea (0.28 g) was added to a refluxing solution of 2-amino-6-chloro-9-(2-benzoyloxyethoxymethyl)purine (1.27 g) in isopropanol (40 ml). The reaction mixture was heated at reflux for 11/2 hours and then chilled. 9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199°-202° C.) was removed by filtration. This was added to 40 ml of aqueous ammonia (about 7 N) and the mixture heated on a steam 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 (0.26 g, m.p. 251°-254° C.).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 11/2 hours
  3. temperaturechilled
  4. custom9-(2-benzoyloxyethoxymethyl)-thioguanine (0.58 g, m.p. 199°-202° C.) was removed by filtration
  5. additionThis was added to 40 ml of aqueous ammonia (about 7 N)
  6. temperaturethe mixture heated on a steam 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

出典と根拠

ORDレコード
ord-0282396aac7e4c6098c5d9a1f7e4280f
出典データセット
uspto-grants-1981_10
特許番号
US04294831

反応ノート

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