N,N-Diethylaniline → 6-Chloro-9H-purine-2,8-diamine

HRID 380333Notes

Reaction equation

HRID 380333 reaction equation
[NH2:1][C:2]1[NH:10][C:9]2[C:8](=O)[NH:7][C:6]([NH2:12])=[N:5][C:4]=2[N:3]=1.C(N(CC)C1C=CC=CC=1)C.P(Cl)(Cl)([Cl:26])=O>>[NH2:12][C:6]1[N:5]=[C:4]2[C:9]([NH:10][C:2]([NH2:1])=[N:3]2)=[C:8]([Cl:26])[N:7]=1

Participants

4

Reactant 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 1354218878-Aminoguanine

Product 1

HCID 158704046-Chloro-9H-purine-2,8-diamine

Procedure

A suspension of 8-aminoguanine (Fischer, Z. Physiol. Chem., 60, 69 (1909); Beaman et al., in Zorback and Tipson, Synthetic Procedures in Nucleic Acid Chemistry, Vol. 1, pp 41-43, John Wiley & Sons, New York, 1968) (3.0 g, 18.1 mmol) in phosphorus oxychloride (90 mL) and N,N-diethylaniline (3 mL) was refluxed for 30 min and the excess phosphorus oxychloride was evaporated under reduced pressure. Ice (20 g) was added slowly to the resulting solution and the pH was adjusted to 6 with a concentrated aqueous sodium hydroxide solution. A yellow solid formed and was collected by filtration, washed with water, and dried to give a green solid. Crystallization from water with charcoal treatment produced 2,8-diamino-6-chloropurine as a white solid: yield, 2.11 g (63%); mp>275° C. dec.; 1H NMR δ 6.09 (s, 2 H, NH2, exchange with D2O), 6.71 (s, 2 H, NH2, exchange with D2O); MS (EI) calcd. m/z for C5H5N635Cl 184.0264, found 184.0266; calcd. m/z C5H5N637Cl 186.0235, found 186.0237.

Workup

  1. customthe excess phosphorus oxychloride was evaporated under reduced pressure
  2. additionIce (20 g) was added slowly to the resulting solution
  3. customA yellow solid formed
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customdried
  7. customto give a green solid
  8. customCrystallization from water with charcoal treatment

Sources & evidence

ORD record
ord-b7fa4496f37e44ddb2929d01e518ed11
Source dataset
uspto-grants-2001_10
Patent number
US06303604B1

Reaction notes

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