Water → 2,4-Dichloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine--hydrogen chloride (1/1)

HRID 2112750Notes

Reaction equation

HRID 2112750 reaction equation
Cl.C([N:9]1[CH2:17][C:16]2[C:15]([Cl:18])=[N:14][C:13]([Cl:19])=[N:12][C:11]=2[CH2:10]1)C1C=CC=CC=1.C(N(CC)CC)C.ClC(OC(Cl)C)=O.O>ClCCCl>[ClH:18].[Cl:19][C:13]1[N:14]=[C:15]([Cl:18])[C:16]2[CH2:17][NH:9][CH2:10][C:11]=2[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 86610780HCID 86610780, compound

Product 1

HCID 446307252,4-Dichloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine--hydrogen chloride (1/1)Yield 54%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Benzyl-2,4-dichloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine hydrochloride (0.500 g, 0.00158 mol) prepared according to Process Step 2 was dissolved in 1,2-dichloroethane (15 mL), and the solution was mixed with triethylamine (0.160 g, 0.00158 mol) added dropwise under ice-cooling. The resulting solution was mixed with 1-chloroethyl chloroformate (0.680 g, 0.00478 mol) added dropwise at room temperature, followed by stirring under reflux for three hours. The reaction mixture was mixed with water (20 mL), followed by shaking and separation. The organic layer was dried over anhydrous magnesium sulfate, and was concentrated under reduced pressure. The residue was dissolved in methanol (15 mL), followed by reflux of the solution for one hour. After standing the reaction mixture to cool, methanol was distilled off under reduced pressure, to thereby yield 2,4-dichloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine hydrochloride (0.19 g, in a yield of 54%).

Workup

  1. additionadded dropwise under ice-
  2. temperaturecooling
  3. additionadded dropwise at room temperature
  4. temperatureunder reflux for three hours
  5. stirringby shaking
  6. customseparation
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationwas concentrated under reduced pressure
  9. dissolutionThe residue was dissolved in methanol (15 mL)
  10. temperatureby reflux of the solution for one hour
  11. temperatureto cool
  12. distillationmethanol was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f668a9317fbd4004b9d6d9388493f9ad
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

Loading…