Phosphorus oxychloride → 2-Amino-4-chloroindolo[2,3-d]pyrimidine hydrochloride

HRID 1358298Notes

Reaction equation

HRID 1358298 reaction equation
[NH2:1][CH:2]1[N:7]=[C:6]2[N:8]=[C:9]3[C:14]([CH:13]=[CH:12][CH:11]=[CH:10]3)=[C:5]2[C:4](=O)[NH:3]1.P(Cl)(Cl)([Cl:18])=O>O1CCOCC1>[ClH:18].[NH2:1][C:2]1[N:3]=[C:4]([Cl:18])[C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 700240322-Amino-4-oxo-3H-indolo[2,3-d]pyrimidine

Product 1

HCID 181843672-Amino-4-chloroindolo[2,3-d]pyrimidine hydrochlorideYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of 2-amino-4-oxo-3H-indolo[2,3-d]pyrimidine (490 mg, 2.5 mmol) and phosphoryl chloride (7 ml, 75 mmol) in dioxane (13 ml) is heated under reflux for 4 hr, then concentrated in vacuo. The residue is triturated with ethanol, filtered, and the solids washed with 10:1 Ethanol:Ethyl Acetate to give 170 mg (27%) 2-amino-4-chloroindolo[2,3-d]pyrimidine hydrochloride as a grey solid, mp >250 C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hr
  3. concentrationconcentrated in vacuo
  4. customThe residue is triturated with ethanol
  5. filtrationfiltered
  6. washthe solids washed with 10:1 Ethanol

Sources & evidence

ORD record
ord-4ff7b8f965bd47a297cf9fa81073b8a7
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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