2-Amino-4,6-dichloropyrimidine → tert-Butyl (4aR*,7aR*)-6-(2-amino-6-chloropyrimidin-4-yl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate

HRID 548936Notes

Reaction equation

HRID 548936 reaction equation
[N:1]1([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5][CH2:4][C@@H:3]2[CH2:7][NH:8][CH2:9][C@H:2]12.CCN(C(C)C)C(C)C.[NH2:26][C:27]1[N:32]=[C:31](Cl)[CH:30]=[C:29]([Cl:34])[N:28]=1>CCO.O>[NH2:26][C:27]1[N:32]=[C:31]([N:8]2[CH2:7][C@@H:3]3[C@@H:2]([N:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5][CH2:4]3)[CH2:9]2)[CH:30]=[C:29]([Cl:34])[N:28]=1

Participants

6

Reactant 3

HCID 655222-Amino-4,6-dichloropyrimidineHCID 81531DiisopropylethylamineHCID 1519436rel-1,1-Dimethylethyl (4aR,7aR)-octahydro-1H-pyrrolo(3,4-b)pyridine-1-carboxylate

Product 1

HCID 58940630tert-Butyl (4aR*,7aR*)-6-(2-amino-6-chloropyrimidin-4-yl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of racemic tert-butyl (4aR*,7aR*)-octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (460 mg, 2.03 mmol) in EtOH (1 mL) containing DIPEA (590 μL, 3.39 mmol) was added a solution of 2-amino-4,6-dichloropyrimidine (277 mg, 169 mmol) in EtOH (9 mL) with stirring and the solution was heated to reflux for 24 hours. The solution was cooled and diluted with water (10 mL) and the resulting solid was collected by filtration, washed with water (20 mL) and dried in vacuo at 60° C. to yield the title compound as a white solid (558 mg, 93%).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe solution was cooled
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with water (20 mL)
  6. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-6769690e67e8482f93f4640c7bf6c4b6
Source dataset
uspto-grants-2011_05
Patent number
US07943628B2

Reaction notes

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