N,N-Dimethylaniline → N'-(6-chloro-7H-purin-2-yl)-N,N-dimethylmethanimidamide

HRID 274322Notes

Reaction equation

HRID 274322 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[NH:7][C:8](=O)[C:9]2[NH:10][CH:11]=[N:12][C:13]=2[N:14]=1)[CH3:3].CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:27])=O.C(=O)([O-])O.[Na+]>>[CH3:1][N:2]([CH:4]=[N:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([Cl:27])[N:7]=1)[CH3:3]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 136087653N-dimethylaminomethyleneguanine

Product 1

HCID 54487942N'-(6-chloro-7H-purin-2-yl)-N,N-dimethylmethanimidamideYield 80%

Conditions

Temperature
80 °C

Procedure

20.6 g (0.1 mol) of N-dimethylaminomethyleneguanine obtained in Example 15, and 12.1 g (0.1 mol) of N,N-dimethylaniline were added to 38.3 g (0.25 mol) of phosphorus oxychloride, followed by stirring at 80° C. for 2 hours. After cooling, the reaction mixture was added to 500 ml of ice water, and then neutralized with 126.0 g (1.5 mol) of sodium hydrogen carbonate. The precipitating crystal was collected by filtration and then washed with 50 ml of water, subsequently with 50 ml of methanol to yield 18.0 g (0.08 mol) of a crystal of 2-dimethylaminomethyleneamino-6-chloropurine (yield 80%). Comparative Example (method disclosed in Japanese Patent Laid-Open No. 227583/1986)

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitating crystal was collected by filtration
  3. washwashed with 50 ml of water, subsequently with 50 ml of methanol

Sources & evidence

ORD record
ord-763198d4ba394d259e9e19873af0caf6
Source dataset
uspto-grants-1995_02
Patent number
US05389637

Reaction notes

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