Chloroform → 2-Anilino-6-chloro-9-(2,3-epoxypropyl)purine

HRID 263939노트

반응식

HRID 263939 반응식
[H-].[Na+].[NH:3]([C:10]1[N:18]=[C:17]2[C:13]([NH:14][CH:15]=[N:16]2)=[C:12]([Cl:19])[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:20]([CH:22]1[O:24][CH2:23]1)Br.C(Cl)(Cl)Cl>C(#N)C>[NH:3]([C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH2:20][CH:22]2[O:24][CH2:23]2)=[C:12]([Cl:19])[N:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 52718829H-Purin-2-amine, 6-chloro-N-phenyl-

생성물 1

HCID 104249662-Anilino-6-chloro-9-(2,3-epoxypropyl)purine수율 34.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Sodium hydride (161 mg, 4 mmol; 60% suspension in mineral oil) was added to a suspension of 2-anilino-6-chloropurine (1 g, 4 mmol; Focher et al. (1988) J. Med. Chem. 31:1496-1500) in anhydrous acetonitrile (240 ml) at room temperature. After stirring for 1 hr epibromohydrin (0.35 ml, 4 mmol) was added, and the suspension was stirred for 48 hr. An equal volume of chloroform was added, and, after filtration through Celite, the filtrate was evaporated to dryness. The residue was chromatographed on silica gel, and the major product was eluted with chloroform to give 417 mg (34% yield) of 2-anilino-6-chloro-9-(2,3-epoxypropyl)purine. 1H NMR δ9.97 (s, 2-NH), 8.24 (s, 8-H), 7.40 (m, C6H5), 4.38 (m, 1'-CH2), 3.45 (m, 2'-CH), 2.72 (m, 3'-CH2). Further elution gave 46 mg (3.8% yield) of the minor 7-isomer.

후처리

  1. additionwas added
  2. filtrationafter filtration through Celite
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was chromatographed on silica gel
  5. washthe major product was eluted with chloroform

출처 및 근거

ORD 기록
ord-b1d5203ab8be4f64b0f7e7d1cc22f826
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646155

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