Water → 2-Chloro-N-(4-chlorophenyl)-9-methyl-9H-purin-6-amine

HRID 2386595Notes

Reaction equation

HRID 2386595 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=O)=[CH:4][CH:3]=1.[H-].[Na+].[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH3:23])=C(Cl)[N:15]=1.O>CN(C)C=O>[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH3:23])=[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 17475N-(4-chlorophenyl)formamideHCID 24758Sodium hydrideHCID 17125532,6-dichloro-9-methyl-9H-purine

Product 1

HCID 592936372-Chloro-N-(4-chlorophenyl)-9-methyl-9H-purin-6-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-(4-Chloro-phenyl)-formamide (766 mg, 4.93 mmol) was dissolved in N,N-dimethylformamide (10 mL). Sodium hydride (60% in mineral oil, 240 mg, 5.91 mmol) was added and the mixture was stirred for 30 min. 2,6-Dichloro-9-methyl-9H-purine (1.0 g, 4.93 mmol) was added and the reaction mixture was heated to 80° C. for 2 hours; cooled to room temperature and poured into water. The resulting precipitate was collected by filtration, washed with water and dried to give (2-chloro-9-methyl-9H-purin-6-yl)-(4-chloro-phenyl)-amine (1.2 g, 4.08 mmol, 83%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-429d6a77d04b4ed09081c90602f6abef
Source dataset
uspto-grants-2012_09
Patent number
US08268838B2

Reaction notes

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