Aniline → 9-Phenyl-2-(3-pyridyl)purine-6-carboxamide

HRID 391617노트

반응식

HRID 391617 반응식
ClC1N=C(C(OC)=O)C([N+]([O-])=O)=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)N=1.Cl[C:23]1[N:28]=[C:27]([C:29]([O:31]C)=O)[C:26]([N+:33]([O-])=O)=[C:25](Cl)[N:24]=1.[NH2:37][C:38]1C=[CH:42][CH:41]=[CH:40][CH:39]=1.C([N:47](C(C)C)CC)(C)C>C1COCC1>[C:16]1([N:15]2[CH:4]=[N:33][C:26]3[C:25]2=[N:24][C:23]([C:41]2[CH:42]=[N:37][CH:38]=[CH:39][CH:40]=2)=[N:28][C:27]=3[C:29]([NH2:47])=[O:31])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 10586879Methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylateHCID 57474557Methyl 2-chloro-5-nitro-6-(phenylamino)pyrimidine-4-carboxylate

생성물 1

HCID 249378619-Phenyl-2-(3-pyridyl)purine-6-carboxamide수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Methyl 2-chloro-5-nitro-6-(phenylamino)pyrimidine-4-carboxylate. A solution of Methyl 2,6-dichloro-5-nitropyrimidine-4-carboxylate (0.72 g, 2.87 mmol) in anhydrous THF (14 mL) was chilled to −78° C. under nitrogen. A solution of aniline (0.288 mL, 3.16 mmol) and diisopropylethylamine (1.50 mL, 8.61 mmol) in anhydrous THF (10 mL) was then added drop wise with stirring over 10 minutes. The reaction was stirred at −78° C. for 1 hour and then allowed to warm to room temperature. After 90 minutes, the solvent was evaporated and the resulting residue purified using chromatography on a normal phase silica gel column (0-10% ethyl acetate in hexanes). Fractions containing product were combined and the solvent evaporated to provide the title compound (0.545 g, 1.76 mmol, 61% yield). MS (ESI) m/z 309.4 [M+1]+.

후처리

  1. stirringThe reaction was stirred at −78° C. for 1 hour
  2. waitAfter 90 minutes
  3. customthe solvent was evaporated
  4. customthe resulting residue purified
  5. additionFractions containing product
  6. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-c1b72cf54f424cadb3e4e0e3802d52a2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383634B2

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