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

HRID 274316Notes

Reaction equation

HRID 274316 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][N:7]([CH3:10])[CH:8]=O.[NH:11]1[C:20](=O)[C:19]2[NH:18][CH:17]=[N:16][C:15]=2[N:14]=[C:12]1[NH2:13].O.C(=O)([O-])O.[Na+]>>[CH3:6][N:7]([CH:8]=[N:13][C:12]1[N:14]=[C:15]2[C:19]([NH:18][CH:17]=[N:16]2)=[C:20]([Cl:3])[N:11]=1)[CH3:10]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 135398634Guanine

Product 1

HCID 54487942N'-(6-chloro-7H-purin-2-yl)-N,N-dimethylmethanimidamide

Conditions

Temperature
100 °C

Procedure

115.0 g (0.75 mol) of phosphorus oxychloride was added to 263.1 g (3.6 mol) of N,N-dimethylformamide, and 45.3 g (0.3 mol) of guanine (manufactured by Sumika Fine Chemicals Co., Ltd.) was then added, followed by stirring at 100° C. for 5 hours. After cooling, the reaction mixture was added to 1500 ml of water containing 315.0 g (3.75 mol) of sodium hydrogen carbonate. The precipitating crystal was collected by filtration and washed with 500 ml of water to yield a crystal of 2-dimethylaminomethyleneamino-6-chloropurine, whose properties are as follows:

Workup

  1. additionwas then added
  2. temperatureAfter cooling
  3. filtrationThe precipitating crystal was collected by filtration
  4. washwashed with 500 ml of water

Sources & evidence

ORD record
ord-6c941af13c20445e89fb3aeb595f766a
Source dataset
uspto-grants-1995_02
Patent number
US05389637

Reaction notes

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