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

HRID 2427952ノート

反応式

HRID 2427952 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-0a6c3577c65e4991a2931623c59ab390
出典データセット
uspto-grants-2011_06
特許番号
US07968556B2

反応ノート

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