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

HRID 2427952Notes

Reaction equation

HRID 2427952 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-0a6c3577c65e4991a2931623c59ab390
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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