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 2416336노트

반응식

HRID 2416336 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-487373f4f06d43f7a7cb0325d46b09e3
출처 데이터셋
uspto-grants-2004_11
특허 번호
US06821980B1

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