Chloroform → 2,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine

HRID 1805869Notes

Reaction equation

HRID 1805869 reaction equation
C([N:8]1[C:16]2[C:15]([Cl:17])=[N:14][C:13]([Cl:18])=[N:12][C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Al+3].[Cl-].[Cl-].[Cl-].C(Cl)(Cl)Cl>ClC1C=CC=CC=1Cl>[Cl:18][C:13]1[N:14]=[C:15]([Cl:17])[C:16]2[NH:8][CH:9]=[CH:10][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6451240Aluminum(III) ChlorideHCID 147277655-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 53750532,4-Dichloro-5H-pyrrolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
160 °C

Procedure

To a suspension of 5-benzyl-2,4-dichloro-5H-pyrrolo[3,2-d]pyrimidine (177 mg, 0.64 mmol) in 1,2-dichlorobenzene (20 mL) was added AlCl3 (852 mg, 6.4 mmol). The reaction mixture was heated at 160° C. for 1.5 h, during which the reaction mixture became dark and homogeneous. Upon completion of the reaction, the reaction mixture was cooled, added CHCl3 and washed with NH4Cl. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Added Hexanes and filtered off the product as purple solids (100 mg, 80%) and used for the next step without further purification.

Workup

  1. customUpon completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. washwashed with NH4Cl
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. filtrationAdded Hexanes and filtered off the product as purple solids (100 mg, 80%)
  9. customused for the next step without further purification

Sources & evidence

ORD record
ord-dca03797087a4c1b9900f3e2da59db8a
Source dataset
uspto-grants-2013_01
Patent number
US08354532B2

Reaction notes

Loading…