Sodium Hydroxide → 4-Chloro-6-(1,2,3,6-tetrahydro-pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 589490Notes

Reaction equation

HRID 589490 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:23][C:17]3[N:18]=[CH:19][N:20]=[C:21]([Cl:22])[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[OH-].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O.O.O>[Cl:22][C:21]1[C:16]2[CH:15]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[NH:23][C:17]=2[N:18]=[CH:19][N:20]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 58709797tert-butyl 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 587100224-Chloro-6-(1,2,3,6-tetrahydro-pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

To a solution of compound Intermediate 1 (2.60 g, 7.77 mmol) in 10 ml DCM, 30 ml TFA/water 95:5 were added. The resulting mixture was stirred at room temperature for 2 hours. The mixture was diluted with water and basified by addition of 2N sodium hydroxide and extracted with DCM. The organic layer was washed with brine (2×), dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on silica (cyclohexane/EtOAc 1:1 to EtOAc) to afford the compound Intermediate 2 as a beige solid.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine (2×)
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica (cyclohexane/EtOAc 1:1 to EtOAc)

Sources & evidence

ORD record
ord-1984b1a35d89477ca6d922a34658adb9
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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