5-(3-Ethoxy-5-hydroxy-4-iodo-benzyl)-pyrimidine-2,4-diamine → Tetrahydropyran-4-sulphonic acid 3'-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-yl ester

HRID 2416336ノート

反応式

HRID 2416336 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([OH:20])[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].C[C:22]([O-])([CH3:24])[CH3:23].[K+].[O:27]1[CH2:32][CH2:31][CH:30]([S:33](Cl)(=[O:35])=[O:34])[CH2:29][CH2:28]1>O1CCCC1>[NH2:10][C:9]1[CH:8]=[C:7]([C:18]2[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]([CH2:7][C:8]3[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)=[CH:16][C:17]=2[O:20][S:33]([CH:30]2[CH2:31][CH2:32][O:27][CH2:28][CH2:29]2)(=[O:35])=[O:34])[CH:24]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 226368575-(3-Ethoxy-5-hydroxy-4-iodo-benzyl)-pyrimidine-2,4-diamineHCID 22637030Oxane-4-sulfonyl chlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 17937307Tetrahydropyran-4-sulphonic acid 3'-amino-4-(2,4-diamino-pyrimidin-5-ylmethyl)-6-ethoxy-biphenyl-2-yl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

5-(3-Ethoxy-5-hydroxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (see example 32 stage a) (2,300 mg; 5.96 mmol) is dissolved in tetrahydrofuran (70 ml), potassium tert-butylate (1,000 mg; 8.9 mmol) is added and the mixture is cooled to −20° C. Tetrahydropyran-4-sulphonyl chloride (2.2 g; 11.9 mmol) is added at this temperature and the mixture is then stirred for one hour at −20° C. The reaction mixture is poured on to ice-water and extracted twice with ethyl acetate. The organic phase is dried over sodium sulphate, the salts are filtered off and the solvent is evaporated off. The residue is chromatographed over silica gel with methylene chloride 1 methanol (19/1) and 0.5% ammonia. The pure fractions are co mbidand the solvent is evaporated off.

後処理

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationthe salts are filtered off
  4. customthe solvent is evaporated off
  5. customThe residue is chromatographed over silica gel with methylene chloride 1 methanol (19/1) and 0.5% ammonia
  6. customis evaporated off

出典と根拠

ORDレコード
ord-487373f4f06d43f7a7cb0325d46b09e3
出典データセット
uspto-grants-2004_11
特許番号
US06821980B1

反応ノート

読み込み中…