Water → 2-Dimethylaminomethyleneamino-6-bromopurine

HRID 274319Notes

Reaction equation

HRID 274319 reaction equation
P(Br)(Br)[Br:2].[CH3:5][N:6]([CH3:9])[CH:7]=O.[NH:10]1[C:19](=O)[C:18]2[NH:17][CH:16]=[N:15][C:14]=2[N:13]=[C:11]1[NH2:12].O.C(=O)([O-])O.[Na+]>>[CH3:5][N:6]([CH:7]=[N:12][C:11]1[N:13]=[C:14]2[C:18]([NH:17][CH:16]=[N:15]2)=[C:19]([Br:2])[N:10]=1)[CH3:9]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 135398634Guanine

Product 1

HCID 540440312-Dimethylaminomethyleneamino-6-bromopurine

Conditions

Temperature
100 °C

Procedure

203.0 g (0.75 mol) of phosphorus tribromide 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 8 hours. After cooling, the reaction mixture was added to 2000 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-bromopurine, 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-7bcd2445c5fd4d7883d610961e9b9b8b
Source dataset
uspto-grants-1995_02
Patent number
US05389637

Reaction notes

Loading…