Imidazole → 2-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide

HRID 391640노트

반응식

HRID 391640 반응식
[NH2:1][C:2]1[C:3]([C:32](OCC)=[O:33])=[N:4][C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][Si](C(C)(C)C)(C)C)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].NC1C(C(OCC)=O)=NC(NC2C=CC=CC=2O)=NC=1NC1C=CC=C[C:46]=1[O:51]C.[Si](Cl)(C(C)(C)C)(C)C.[NH:74]1C=CN=C1>C(Cl)Cl>[OH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:5]1[N:6]=[C:7]2[C:2]([NH:1][C:46](=[O:51])[N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:3]([C:32]([NH2:74])=[O:33])[N:4]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57474631Ethyl 5-amino-2-(2-hydroxyphenylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylateHCID 57474634Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenyl amino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate

생성물 1

HCID 249381082-(2-Hydroxyphenylamino)-9-(2-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carboxamide수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl 5-amino-2-(2-(tert-butyldimethylsilyloxy)phenylamino)-6-(2-methoxyphenyl amino)pyrimidine-4-carboxylate. Ethyl 5-amino-2-(2-hydroxyphenylamino)-6-(2-methoxy phenylamino)pyrimidine-4-carboxylate (184 mg, 0.465 mmol) was dissolved in methylene chloride (5 mL) and tert-butyldimethylsilyl chloride (77 mg, 0.512 mmol) and imidazole (38.0 mg, 0.558 mmol) were added. The reaction mixture was stirred overnight at room temperature. Solvent was removed under reduced pressure and crude was purified by column chromatography (20% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (232.6 mg, 0.456 mmol, 98% yield) as a yellow solid. MS (ESI) m/z 510.5 [M+1]+.

후처리

  1. customSolvent was removed under reduced pressure and crude
  2. customwas purified by column chromatography (20% ethyl acetate in hexanes)
  3. additionFractions containing product
  4. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-56b160d05c1e4342adb97f140d24a397
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383634B2

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